β-Keto sulfones: Preparation and application in organic synthesis

Journal of Sulfur Chemistry

Volumn 35, Issue 2, 2014, Pages 188-236

  Markitanov, Yuriy M ^a   Timoshenko, Vadim M ^a   Shermolovich, Yuriy G ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

? keto sulfone; alkylation; carbonyl; cyclization; desulfonylation; heterocycle; methylene; Michael addition; multicomponent reaction; reduction; sulfonyl

Indexed keywords

ADDITION REACTIONS; CYCLIZATION;

% REDUCTIONS; ?-KETO SULPHONE; CYCLIZATIONS; DESULFONYLATION; HETEROCYCLES; KETO SULFONES; METHYLENE; MICHAEL ADDITIONS; MULTICOMPONENT REACTION; MULTICOMPONENTS; SULFONYL; [CARBONYL;

REACTION INTERMEDIATES;

EID: 84891859115     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415993.2013.815749     Document Type: Review

References (200)

1. Simpkins NS. Sulfones in organic synthesis. Oxford: Pergamon Press; 1993.
2. Shyshkina OO, Popov KS, Gordivska OO, Tkachuk TM, Kovalenko NV, Volovnenko TA, Volovenko YM. Synthesis and chemical properties of cyclic β-keto sulfones. Chem Heterocycl Compd. 2011; 47: 923-945. doi: 10.1007/s10593-011-0858-1
3. House HO, Larson JK. The use of β-ketone sulfones as synthetic intermediates. J Org Chem. 1968; 33: 61-65. doi: 10.1021/jo01265a012
4. Tomsen MW, Handwerker BM, Katz SA, Belser RB. Preparation of β-keto sulfones from [(phenylsulfonyl)methylene]dilithium and acid chlorides. J Org Chem. 1988; 53: 906-907. doi: 10.1021/jo00239a051
5. Wildeman J, Van Leusen AM. Convenient alternative synthesis of sulfones in aprotic medium using phase-transfer catalysis. Synthesis. 1979; 733-734. doi: 10.1055/s-1979-28819
6. Vennstra GE, Zwaneburg B. An improved synthesis of sulfones using tetrabutyl-ammonium sulfinates. Synthesis. 1975; 519-520. doi: 10.1055/s-1975-23829
7. Fan A-L, Cao S, Zhang Z. A new approach for the synthesis of some 1,4-benzoxathiin 4,4-dioxide derivatives. J Heterocycl Chem. 1997; 34: 1657-1660. doi: 10.1002/jhet.5570340603
8. Katritzky AR, Abdel-Fattah AAA, Wang M. Efficient conversion of sulfones into β-keto sulfones by N-acylbenzotriazoles. J Org Chem. 2003; 68: 1443-1446. doi: 10.1021/jo026636l
9. Pospíšil J, Sato H. Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones. J Org Chem. 2011; 76: 2269-2272. doi: 10.1021/jo102326p
10. Kamijo S, Dudley GB. Claisen-type condensation of vinylogous acyl triflates. Org Lett. 2006; 8: 175-177. doi: 10.1021/ol0527781
11. Mueller P, Bolea C. The enantioselectivity and the stereochemical course of copper-catalyzed intramolecular CH insertions of phenyliodonium ylides. Helv Chim Acta. 2002; 85: 483-494. doi: 10.1002/1522-2675(200202)85:2<483::AID- HLCA483>3.0.CO;2-Q
12. Field L, Lawson J, McFarland J. Grignard reagents of sulfones. IV. Reactions with nitriles, esters and an isocyanate. J Am Chem Soc. 1956; 78: 4389-4394. doi: 10.1021/ja01598a054
13. Yoshimatsu M, Oh-Ishi K, Tanabe G, Muraoka O. The first isolation and characterization of sulfonylbuta-1,3-diynes. J Chem Soc, Perkin Trans. 2002; 1: 1413-1416. doi: 10.1039/b203913n
14. Kreis M, Nieger M, Bräse S. Synthesis of novel planar-chiral [2.2]paracyclophane derivatives as potential ligands for asymmetric catalysis. J Organomet Chem. 2006; 691: 2171-2181. doi: 10.1016/j.jorganchem.2005.10.031
15. Suryakiran N, Reddy TS, Ashalatha K, Lakshman M, Venkateswarlu Y. Facile polyethylene glycol (PEG-400) promoted synthesis of β-ketosulfones. Tetrahedron Lett. 2006; 47: 3853-3856. doi: 10.1016/j.tetlet.2006.03.181
16. Guravaiah N, Rao VR. Facile polyethylene glycol (PEG-400) promoted synthesis of some new heteryl (E)-styryl sulfones. J Chem Res. 2009; 237-239. doi: 10.3184/030823409X430176
17. Kumar A, Muthyala MK. 1-Butyl-3-methylimidazolium p-toluenesulfinate: a novel reagent for synthesis of sulfones and β-ketosulfones in ionic liquid. Tetrahedron Lett. 2011; 52: 5368-5370. doi: 10.1016/j.tetlet.2011.08.035
18. Hu Y, Chen Z-C, Le Z-G, Zheng Q-G. Organic reactions in ionic liquids: an efficient method for the synthesis of aryl sulfones by alkylation of sodium arenesulfinates with alkyl halides. J Chem Res. 2004;2004; 267-269. doi: 10.3184/0308234041209031
19. Suryakiran N, Prabhakar P, Rajesh K, Suresh V, Venkateswarlu Y. Synthesis of β-keto-sulfones using ionic liquid [TPA][Pro] as an efficient and reusable reaction medium. J Mol Catal A. 2007; 270: 201-204. doi: 10.1016/j.molcata.2007.01.049
20. Guravaiah N, Rao VR. Solvent-free synthesis of new heteryl β-ketosulfones. J Chem Res. 2009; 2009: 87-89. doi: 10.3184/ 030823409X401745
21. Xiang J, Ipek M, Suri V, Tam M, Xing Y, Huang N, Zhang Y, Tobin J, Mansour TS, McKew J. β-Keto sulfones as inhibitors of 11β- hydroxysteroid dehydrogenase type I and the mechanism of action. Bioorg Med Chem. 2007; 15: 4396-4405. doi: 10.1016/j.bmc.2007.04.035
22. Curti C, Laget M, Carle AO, Gellis A, Vanelle P. Rapid synthesis of sulfone derivatives as potential anti-infectious agents. Eur J Med Chem. 2007; 42: 880-884. doi: 10.1016/j.ejmech.2006.12.015
23. Barnes KD, Ward R. Synthesis of 2-aryl-3-trifluoromethylsulfonylpyrroles. J Heterocycl Chem. 1995; 32: 871-874. doi: 10.1002/jhet.5570320333
24. Eugene F, Langlois B, Laurent E. Improved synthesis for the preparation of trifluoromethyl sulfones used as intermediates of di- or tri-substituted olefins. J Fluorine Chem. 1994; 66: 301-309. doi: 10.1016/0022-1139(93)02909-X
25. Xie Y-Y, Chen Z-C. Hypervalent iodine in synthesis. 66. One pot preparation of β-keto sulfones by reaction of ketones, [hydroxy(tosyloxy) iodo] benzene, and sodium sulfinates. Synth Commun. 2001; 31: 3145-3149. doi: 10.1081/SCC-100105890
26. Kumar D, Sundaree S, Rao VS, Varma RS. A facile one-pot synthesis of β-keto sulfones from ketones under solvent-free conditions. Tetrahedron Lett. 2006; 47: 4197-4199. doi: 10.1016/j.tetlet.2006.04.076
27. Trost BM. -Sulfenylated carbonyl compounds in organic synthesis. Chem Rev. 1978; 78: 363-382.
28. Morais GR, Humphrey AJ, Falconer RA. Application of HOF·CH 3CN to the synthesis of glycosyl sulfones. Tetrahedron. 2008; 64: 7426-7431. doi: 10.1016/j.tet.2008.05.033
29. Bera S, Pathak T. Synthesis and reactions of allenic sulfone-modified thymidine: the first allenic sulfone to alkylate deoxyadenosine. Synlett. 2004; 2147-2150.
30. Gueyrard D, Fontaine P, Goekjian P. Synthesis of C-glucoside endo-glycals from c -glucosyl vinyl sulfones. Synthesis. 2006; 1499-1503. doi: 10.1055/s-2006-926422
31. Frydman N, Mazur Y. Free-radical rearrangement of enol sulfonates. J Am Chem Soc. 1970; 92: 3203-3205. doi: 10.1021/ja00713a058
32. Holmquist CR, Roskamp EJ. Tin(II) chloride catalyzed addition of diazo sulfones, diazo phosphine oxides, and diazo phosphonates to aldehydes. Tetrahedron Lett. 1992; 33: 1131-1134. doi: 10.1016/S0040-4039(00)91877-X
33. Kamigata N, Udodaira K, Shimizu T. Reactions of sulfonyl chlorides with silyl enol ethers catalysed by a ruthenium(II) phosphine complex: convenient synthesis of β-keto sulfones. J Chem Soc, Perkin Trans. 1997; 1: 783-786. doi: 10.1039/a604466b
34. Bouchez L, Vogel P. One-pot, three-component synthesis of open-chain, polyfunctional sulfones. Synthesis. 2002; 225-231. doi: 10.1055/s-2002-19797
35. Wang L, Zhang Y. Indium-mediated coupling reaction of sulfonyl chlorides with alkyl bromides in water. A facile synthesis of sulfones. J Chem Res Synop. 1998; 588-589. doi: 10.1039/a803996h
36. Li H, Wang H, Pan Y, Shi Y. A new synthetic route to sulfones via activated nickel-assisted reactions of arenesulfonyl chlorides with active halides. Synth Commun. 1998; 28: 409-415. doi: 10.1080/00397919808005094
37. Srinivas K, Dubey PK. Zinc-mediated tandem-one-pot facile synthesis of 1-(arylsulfonyl) aryl/heteryl methanes: a case of C=S bond formation. Synth Commun. 2011; 41: 1584-1592. doi: 10.1080/00397911.2010.488310
38. Zhang J, Zhang Y. Synthesis of sulfones from arenesulfonyl chlorides and alkyl halides using the Sm/HgCl 2 bimetallic system. J Chem Res Synop. 2001; 2001: 516-517(2). doi: 10.3184/030823401103168929
39. Ramaiah K, Dubey PK, Ramanatham J. A facile phase-transfer synthesis of some β-keto sulfones. Indian J Chem Sect B. 1999; 38: 297-301.
40. Huang X, Pi J-H. A Novel synthesis of sulfones via the o,o-diethylphosphorotellurite ion-assisted coupling of arenesulfonyl chlorides with active halides. Synth Commun. 1990; 20: 2291-2295. doi: 10.1080/00397919008053171
41. Lai C, Xi C, Jiang Y, Hua R. One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water. Tetrahedron Lett. 2005; 46: 513-515. doi: 10.1016/j.tetlet.2004.10.176
42. Sreedhar B, Rawat V. A regioselective catalyst- and additive-free synthesis of β-keto sulfones from aryl acetylenes and sodium arenesulfinates. Synlett. 2012; 413-417. doi: 10.1055/s-0031-1290318
43. Qian H, Huang X. Solid-phase synthesis of β-keto sulfones. Synthesis. 2006; 1934-1936.
44. Samakkanad N, Katrun P, Techajaroonjit T, Hlekhlai S, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. IBX/I 2-Mediated reaction of sodium arenesulfinates with alkenes: facile synthesis of β-keto sulfones. Synthesis. 2012; 1693-1699.
45. Srinivasa Reddy N, Premkumar Reddy E, Ramana Reddy MV. Solvent dependent dehydrating condensation of benzylsulfonyl acetic acids. Synth Commun. 2004; 34: 2691-2695. doi: 10.1081/SCC-200025638
46. Tsui GC, Glenadel Q, Lau C, Lautens M. Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of (Z)-β-sulfonylvinylamines and β-keto sulfones. Org Lett. 2011; 13: 208-211. doi: 10.1021/ol102598p
47. Truce WE, Bannister WW, Knospe RH. The preparation of β-keto sulfones by the thorpe reaction. The acidity of β-keto sulfones. J Org Chem. 1962; 27: 2821-2828. doi: 10.1021/jo01055a025
48. Kada R, Knoppová V, Jurášek A, Kováč J. Furan derivatives-LXXVII: synthesis and study of sulphides and sulphones of 5-nitrofuran series. Tetrahedron. 1976; 32: 1411-1414. doi: 10.1016/0040- 4020(76)85021-1
49. Bordwell FG. Equilibrium acidities in dimethyl sulfoxide solution. Acc Chem Res. 1988; 21: 456-463. doi: 10.1021/ar00156a004
50. Holst EH, Fernelius WC. Some properties of β-ketosulfones and β-disulfones. J Org Chem. 1958; 23: 1881-1883. doi: 10.1021/jo01106a014
51. Kohler E, Potter H. The acylation and alkylation of β-diketones and β-sulfonyl ketones. J Am Chem Soc. 1936; 58: 2166-2170. doi: 10.1021/ja01302a023
52. Villemin D, Alloum AB. Dry reaction under microwave: condensation of sulfones with aldehydes on KF-Alumina. Synth Commun. 1991; 21: 63-68. doi: 10.1080/00397919108020790
53. Li Q-S, Li C-Y, Lu X, Zhang H, Zhu H-L. Design, synthesis and biological evaluation of novel (E)-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors. Eur J Med Chem. 2012; 50: 288-295. doi: 10.1016/j.ejmech.2012.02.007
54. Bogdanowicz-Szwed K, Pałasz A. Polycyclic 2H-pyran derivatives by intramolecular hetero-diels-alder reactionsof -sulfur-substituted , β-unsaturated carbonyl compounds. Monatsh Chem. 2001; 132: 393-401. doi: 10.1007/s007060170125
55. Xing C, Zhu S. Unexpected formation of tetrasubstituted 2,3-dihydrofurans from the reactions of β-keto polyfluoroalkanesulfones with aldehydes. J Org Chem. 2004; 69: 6486-6488. doi: 10.1021/jo049317y
56. Xing C, Li X, Zhu S, Zhao J, Zhu S. Synthesis and hetero-Diels-Alder reactions of (E)-perfluoroalkanesulfonyl-,β-unsaturated ketones. Tetrahedron Lett. 2006; 47: 4951-4955. doi: 10.1016/j.tetlet.2006.04.156
57. Yang J, Li H, Li M, Peng J, Gu Y. Multicomponent reactions of β-ketosulfones and formaldehyde in a bio-based binary mixture solvent system composed of meglumine and gluconic acid aqueous solution. Adv Synth Catal. 2012; 354: 688-700. doi: 10.1002/adsc.201100799
58. Santilli AA, Rosenberg MD, Osdene TS, Childress SJ. Synthesis of amino-5-arylsulfonylpyrimidines. J Heterocycl Chem. 1971; 8: 975-982. doi: 10.1002/jhet.5570080615
59. Neplyuev VN, Sinenko TA, Pel'kis PS. Zh Org Khim. (Russ.) 1977; 13: 1341-1345.
60. Reiter LA. Synthesis of 2-substituted 5-acetyl-1(H)-imidazoles via 3-chloro-4,4-dimethoxy-2-butanone and related 3,4-disubstituted 3-buten-2-ones. J Org Chem. 1984; 49: 3494-3498. doi: 10.1021/jo00193a012
61. Riahi A, Shkoor M, Fatunsin O, Lubbe M, Reinke H, Langer P. First synthesis of 4-(arylsulfonyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 2-arylsulfonyl-3-ethoxy-2-en-1-ones. Tetrahedron Lett. 2009; 50: 115-117. doi: 10.1016/j.tetlet.2008.10.097
62. Shkoor M, Riahi A, Fatunsin O, Reinke H, Fischer C, Langer P. Diversity-oriented synthesis of functionalized diaryl sulfones by regioselective [3+3] cyclizations of 1,3-bis(siloxy)buta-1,3-dienes with 2-(arylsulfonyl)-3- ethoxy-2-en-1-ones: Scope and limitations. Synthesis. 2009; 2223-2235.
63. Lemcke T, Messinger P. Sulfonylsubstituierte Heterocyclen aus β-Oxo-β-sulfonyl-enolethern und Amidinen, Hydrazinen oder Hydroxylamin. Arch Pharm. 1995; 328: 269-270. doi: 10.1002/ardp.19953280312
64. Shaaban MR, Saleh TS, Mayhoub AS, Mansour A, Farag AM. Synthesis and analgesic/anti-inflammatory evaluation of fused heterocyclic ring systems incorporating phenylsulfonyl moiety. Bioorg Med Chem. 2008; 16: 6344-6352. doi: 10.1016/j.bmc.2008.05.011
65. Takahashi M, Mamiya T, Wakao M. Preparation of 5-sulfonylpyrimidines from β-keto, β-cyano-, and β-ethoxycarbonyl-β-sulfonylenamines. J Heterocycl Chem. 1986; 23: 77-80. doi: 10.1002/jhet.5570230116
66. Abu-Shanab FA. Synthesis of polyfunctionally substituted pyridine-2-(1H)-thiones containing a sulfone moiety. J Sulfur Chem. 2006; 27: 433-440. doi: 10.1080/17415990600875327
67. Elkholy YM, Abu-Shanab FA, Erian AW. Studies with pyridinethiones: a convenient synthesis of polyfunctionally substituted pyridine ring systems. Phosphorus Sulfur Silicon Relat Elem. 2000; 167: 151-159. doi: 10.1080/10426500008082395
68. Barroso S, Blay G, Al-Midfa L, Muñoz MC, Pedro JR. Copper(II)-bis(oxazoline) catalyzed asymmetric Diels-Alder reaction with -arylsulfonyl enones as dienophiles. J Org Chem. 2008; 73: 6389-6392. doi: 10.1021/jo8009227
69. O'Sullivan WI, Tavares DF, Hauser CR. Some condensations at the methylene and terminal methyl groups of benzenesulfonylacetone through its mono- and dipotassio salts. J Am Chem Soc. 1961; 83: 3453-3457. doi: 10.1021/ja01477a025
70. Giovannini R, Petrini M. Ruthenium tetroxide catalyzed oxidations of 3-alkyl-4-(2-furyl)-4-oxobutanenitriles: synthesis of methyl 2-alkyl-3-cyanopropanoates. Tetrahedron Lett. 1997; 38: 3781-3784. doi: 10.1016/S0040-4039(97)00734-X
71. Harmata M, Wacharasindhu S. Addition of functionalized nucleophiles to a bridgehead bromoketone. Synthesis. 2007; 2365-2369. doi: 10.1055/s-2007-983775
72. Coia N, Bouyssi D, Balme G. Efficient, transition metal mediated, sequential, two- and three-component coupling reactions for the synthesis of highly substituted five-membered ring carbocycles. Eur J Org Chem. 2007; 3158-3165. doi: 10.1002/ejoc.200700197
73. Curti C, Crozet MD, Vanelle P. Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones. Tetrahedron. 2009; 65: 200-205. doi: 10.1016/j.tet.2008.10.080
74. Zhou Q-F, Yang F, Guo Q-X, Xue S. DMAP-catalyzed benzannulation of ethyl propiolate with β-dicarbonyl moieties. Synlett. 2007; 2073-2076.
75. Patil NT, Kadota I, Shibuya A, Gyoung YS, Yamamoto Y. Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst. Adv Synth Catal. 2004; 346: 800-804. doi: 10.1002/adsc.200404046
76. Patil NT, Pahadi NK, Yamamoto Y. An improved catalytic system, Pd(PPh 3) 4/PhCOOH combined catalyst, for the allylation of carbon pronucleophiles with allenes. Synthesis. 2004; 2186-2190.
77. Patil NT, Yamamoto Y. Direct allylic substitution of allyl alcohols by carbon pronucleophiles in the presence of a palladium/carboxylic acid catalyst under neat conditions. Tetrahedron Lett. 2004; 45: 3101-3103. doi: 10.1016/j.tetlet.2004.02.094
78. Manabe K, Kobayashi S. Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water. Org Lett. 2003; 5: 3241-3244. doi: 10.1021/ol035126q
79. Slatford PA, Whittlesey MK, Williams JMJ. C-C Bond formation from alcohols using a Xantphos ruthenium complex. Tetrahedron Lett. 2006; 47: 6787-6789. doi: 10.1016/j.tetlet.2006.07.069
80. Kashin AN, Mitin AV, Beletskaya IP, Wife R. Palladium-catalyzed arylation of sulfonyl CH-acids. Tetrahedron Lett. 2002; 43: 2539-2542. doi: 10.1016/S0040-4039(02)00321-0
81. Muxworthy JP, Wilkinson JA, Procter G. Stereoselective cycloadditions of chiral acyl-nitroso compounds; unexpected formation of an oxazolidinone. Tetrahedron Lett. 1995; 36: 7539-7540. doi: 10.1016/0040-4039(95)01526-4
82. Kinoshita H, Hayashi Y, Murata Y, Inomata K. Convenient and regioselective syntheses of 3,4-disubstituted Δ 3-pyrrolin-2-one derivatives starting from 2-tosyl-3,4-disubstituted pyrroles. Chem Lett. 1993; 22: 1437-1440. doi: 10.1246/cl.1993.1437
83. Michael JP, de Koning CB, Malefetse TJ, Yillah I. Preparation and reductive transformations of vinylogous sulfonamides (β-sulfonyl enamines), and application to the synthesis of indolizidines. Org Biomol Chem. 2004; 2: 3510-3517. doi: 10.1039/b413379j
84. Tobrmanová M, Tobrman T, Dvořák D. Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: route to (E)-alkenylpurines. Collect Czech Chem Commun. 2011; 76: 311-326. doi: 10.1135/cccc2011030
85. Kim JN, Im YJ, Kim JM. Synthesis of ortho-hydroxyacetophenone derivatives from Baylis-Hillman acetates. Tetrahedron Lett. 2002; 43: 6597-6600. doi: 10.1016/S0040-4039(02)01441-7
86. Kim SH, Kim KH, Kim HS, Kim JN. Regioselective synthesis of 1,2,4,5-tetrasubstituted pyridines from Baylis-Hillman adducts via consecutive [3+2+1] annulation protocol. Tetrahedron Lett. 2008; 49: 1948-1951. doi: 10.1016/j.tetlet.2008.01.110
87. Im Y-J, Chung Y-M, Gong J-H, Kim J-N. Synthesis of naphthalenes from the reaction of Baylis-Hillman acetates and sulfonyl group-containing active methylene compounds. Bull Korean Chem Soc. 2002; 23: 787-788. doi: 10.5012/bkcs.2002.23.6.787
88. Fesenko AA, Shutalev AD. New approach to 5-arylsulfonyl-substituted 1,2-dihydropyrimidin-2-ones via base-induced chloroform elimination from 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. Tetrahedron. 2010; 66: 7219-7226. doi: 10.1016/j.tet.2010.06.058
89. Tennant G, Wallis C, Weaver G. A new synthesis of substituted imidazo pyridinones by reductive cyclisation of 4-nitro-1H-imidazol-5-yl di-and tri-carbonyl compounds. J Chem Soc, Perkin Trans. 1999; 1: 629-640. doi: 10.1039/a808202b
90. Hanessian S, Johnstone S. Synthesis of hydroxamic esters via alkoxyaminocarbonylation of β-dicarbonyl compounds. J Org Chem. 1999; 64: 5896-5903. doi: 10.1021/jo990353k
91. Basheer A, Rappoport Z. Substituted 2-methylene-1,3-oxazolidines, -1,3-thiazolidines, -1,3-benzothiazines, -1,3-oxazines, and substituted imidazopyrimidinediones from Cl(CH 2) n NCO and Cl(CH 2) n NCS and active methylene compounds. J Org Chem. 2006; 71: 9743-9750. doi: 10.1021/jo061835g
92. Sherif SM. A convenient synthesis of polyfunctionally substituted 2-(arolyl-(arylsulfonyl)-methylene)-2,3-dihydrothiazoles and -thiazolidin-4-ones and their fused derivatives. Monatsh Chem. 1996; 127: 557-568. doi: 10.1007/BF00807081
93. Dawood K, Kheder N, Ragab E, Mohamed S. A facile access to some new pyrazole, 1,3,4-thiadiazole, and thiophene derivatives via β-ketosulfones. Phosphorus Sulfur Silicon Relat Elem. 2010; 185: 330-339. doi: 10.1080/10426500902796980
94. Voronkova V, Baranin S. Diaminomethylidene derivatives of β-oxo sulfones as potential reagents in heterocyclic synthesis and chelating ligands. Russ Chem Bull. 2010; 59: 1887-1895.
95. Flynn CJ, Elcoate CJ, Lawrence SE, Maguire AR. Highly enantioselective intramolecular copper catalyzed C-H insertion reactions of -diazosulfones. J Am Chem Soc. 2010; 132: 1184-1185. doi: 10.1021/ja909713a
96. Wurz RP, Lin W, Charette AB. Trifluoromethanesulfonyl azide: an efficient reagent for the preparation of -cyano-diazo carbonyls and an -sulfonyl-diazo carbonyl. Tetrahedron Lett. 2003; 44: 8845-8848. doi: 10.1016/j.tetlet.2003.09. 197
97. Chiara JL, Suárez JR. Synthesis of -diazo carbonyl compounds with the shelf-stable diazo transfer reagent nonafluorobutanesulfonyl azide. Adv Synth Catal. 2011; 353: 575-579. doi: 10.1002/adsc.201000846
98. Pang W, Zhu S, Xing C, Luo N, Jiang H, Zhu S. Synthesis of stable arsonium and sulfur ylides from perfluoroalkanesulfonyl diazocarbonyl compounds and their X-ray diffraction analysis. J Fluorine Chem. 2008; 129: 343-348. doi: 10.1016/j.jfluchem.2008.01.007
99. Muthyala MK, Choudhary S, Kumar A. Synthesis of ionic liquid-supported sulfonyl azide and its application in diazotransfer reaction. J Org Chem. 2012; 77: 8787-8791. doi: 10.1021/jo301529b
100. Takeda H, Nakada M. Studies on the structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of -diazo-β-keto sulfones possessing a methyl-substituted phenyl group. Tetrahedron Asymm. 2006; 17: 2896-2906. doi: 10.1016/j.tetasy.2006.10.046
101. Shi B, Blake AJ, Lewis W, Campbell IB, Judkins BD, Moody CJ. Rhodium carbene routes to oxazoles and thiazoles. Catalyst effects in the synthesis of oxazole and thiazole carboxylates, phosphonates, and sulfones. J Org Chem. 2010; 75: 152-161. doi: 10.1021/jo902256r
102. Abdelhamid AO, Zohdi HF, Sallam MMM, Ahmed NA. Reactions with hydrazonoyl halides. Part 27: synthesis of some new triazolo[4,3-a]benzimidazole and unsymmetrical azine derivatives. Phosphorus Sulfur Silicon Relat Elem. 2000; 164: 181-188. doi: 10.1080/10426500008045244
103. Grossert JS, Dubey PK, Gill GH, Cameron TS, Gardner PA. The preparation, spectral properties, structures, and base-induced cleavage reactions of some -halo-β-ketosulfones. Can J Chem. 1984; 62: 798-807. doi: 10.1139/v84-133
104. Bhingolikar V, Mahalle S. Rapid and convenient synthetic strategy for 2-amino-4-aryl-5-aryl-sulfonyl thiazoles. Indian J Chem Sect B. 2005; 44: 2589-2593.
105. Suryakiran N, Prabhakar P, Srikanth Reddy T, Chinni Mahesh K, Rajesh K, Venkateswarlu Y. Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones. Tetrahedron Lett. 2007; 48: 877-881. doi: 10.1016/j.tetlet.2006.11.129
106. Suryakiran N, Srikanth Reddy T, Suresh V, Lakshman M, Venkateswarlu Y. Synthesis of -iodo β-ketosulfones and -iodo methylsulfones using iodine monochloride. Tetrahedron Lett. 2006; 47: 4319-4323. doi: 10.1016/j.tetlet.2006. 04.123
107. Suryakiran N, Srikanth Reddy T, Venkateswarlu Y. Iodination of β-keto-sulfones using molecular iodine and hydrogen peroxide in aqueous medium: facile synthesis of -iodomethyl sulfones. J Sulfur Chem. 2007; 28: 471-476. doi: 10.1080/17415990701595865
108. Nie J, Sonoda T, Kobayashi H. Synthesis of new polyfluorinated nitrogen acids bis (polyfluoroalkoxy) sulfony lamines. J Fluorine Chem. 1998; 87: 45-47. doi: 10.1016/S0022-1139(97)00103-6
109. TM F-TEDA-BF 4. Tetrahedron. 2008; 64: 7419-7425. doi: 10.1016/j.tet.2008.05.034
110. Kumar D, Sundaree MS, Patel G, Rao VS, Varma RS. Solvent-free facile synthesis of novel -tosyloxy β-keto sulfones using [hydroxy(tosyloxy)iodo] benzene. Tetrahedron Lett. 2006; 47: 8239-8241. doi: 10.1016/j.tetlet.2006.09. 107
111. Kiren S, Padwa A. A benzannulation protocol to prepare substituted aryl amines using a Michael-aldol reaction of β-keto sulfones. J Org Chem. 2009; 74: 7781-7789. doi: 10.1021/jo9017793
112. Shirakawa S, Shimizu S. Hydrogen-bond-promoted C-C bond-forming reaction: catalyst-free Michael addition reactions in ethanol. Synlett. 2007; 3160-3164. doi: 10.1055/s-2007-992377
113. Velikorodov A, Mochalin V. Reactions of N, N-Bis (methoxycarbonyl)-p- benzoquinonediimine with β-Tosyl Carbonyl Compounds. Russ J Org Chem. 2001; 37: 1054-1055. doi: 10.1023/A:1012407423432
114. Attanasi OA, Favi G, Filippone P, Perrulli FR, Santeusanio S. A novel and convenient protocol for synthesis of pyridazines. Org Lett. 2009; 11: 309-312. doi: 10.1021/ol802432z
115. Lachia M, Iriart S, Baalouch M, De Mesmaeker A, Beaudegnies R. Ethyl-2-(2-chloroethyl)acrylate: a new very versatile -cyclopropylester cation synthon. Efficient synthesis of cyclopropane ester derivatives by Michael addition-induced cyclization reaction. Tetrahedron Lett. 2011; 52: 3219-3222. doi: 10.1016/j.tetlet.2011.04.046
116. Lin H, Shen Q, Lu L. β-(Trifluoromethyl)vinyl sulfonium salts: preparation and reactions with active methylene and methenyl compounds. J Org Chem. 2011; 76: 7359-7369. doi: 10.1021/jo2009033
117. Deng J, Wang F, Yan W, Zhu J, Jiang H, Wang W, Li J. Synthesis of 3-substituted 1,5-aldehyde esters via an organocatalytic highly enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals. Chem Commun. 2012; 48: 148-150. doi: 10.1039/c1cc15714k
118. Alemán J, Marcos V, Marzo L, García Ruano JL. Influence of the reaction conditions on the evolution of the Michael addition of β-keto sulfones to ,β-unsaturated aldehydes. Eur J Org Chem. 2010; 4482-4491.
119. Pulkkinen J, Aburel PS, Halland N, Jørgensen KA. Highly enantio- and diastereoselective organocatalytic domino Michael-aldol reactions of β-diketone and β-ketosulfone nucleophiles with ,β-unsaturated ketones. Adv Synth Catal. 2004; 346: 1077-1080. doi: 10.1002/adsc.200404115
120. Sun X, Yu F, Ye T, Liang X, Ye J. Catalytic asymmetric Michael reactions of ,β-unsaturated ketones with sulfonyl-containing nucleophiles: chiral synthesis of (R)-muscone and (S)-celery ketone. Chem Eur J. 2011; 17: 430-434. doi: 10.1002/chem.201002418
121. Enders D, Grossmann A, Huang H, Raabe G. Dual secondary amine/N-heterocyclic carbene catalysis in the asymmetric Michael/cross-benzoin cascade reaction of β-oxo sulfones with enals. Eur J Org Chem. 2011; 4298-4301. doi: 10.1002/ejoc.201100690
122. García Mancheño O, Tangen P, Rohlmann R, Fröhlich R, Alemán J. Synthesis of chiral cyclic nitrones by asymmetric addition of β-ketosulfones to nitroalkenes followed by reductive cyclization. Chem Eur J. 2011; 17: 984-992. doi: 10.1002/chem.201001914
123. Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Asymmetric organocatalysis with sulfones. Angew Chem Int Ed. 2010; 49: 2668-2679.
124. Nájera C, Yus M. Desulfonylation reactions: recent developments. Tetrahedron. 1999; 55: 10547-10658. doi: 10.1016/S0040-4020(99)00600-6
125. Kondo K, Tunemoto D. Sulfonyl carbanions in synthesis. II. A novel synthesis of 1,4-dicarbonyl systems. Tetrahedron Lett. 1975; 16: 1397-1400. doi: 10.1016/S0040-4039(00)72152-6
126. Guo H, Zhang Y. A convenient method for the reductive desulfonylation of some sulfones by the Sm/HOAc system. J Chem Res Synop. 2001; 2001: 26-27(2). doi: 10.3184/030823401103168172
127. Benedetti F, Berti F, Risaliti A. Cyclization of γ,δ -epoxy-cyanosulphones. A simple, diastereoselective route to cyclopropane carboxylic acids. Tetrahedron Lett. 1993; 34: 6443-6446. doi: 10.1016/0040-4039(93)85066-6
128. ′ keto-methylene tri-peptide isosteres incorporating phenylalanine, tyrosine and valine units. Tetrahedron Lett. 1995; 36: 3577-3580. doi: 10.1016/0040-4039(95) 00564-S
129. Huang X, Pi J-H. Desulfonylation of -alkyl-β-keto-sulfones by sodium hydrogen telluride under PTC conditions. Synth Commun. 1990; 20: 2297-2300. doi: 10.1080/00397919008053172
130. Guo H, Ye S, Wang J, Zhang Y. Reductive desulfonylation of β-ketosulfones by TiCl 4-Zn. J Chem Res Synop. 1997; 114-114. doi: 10.1039/a606405a
131. Smith AB, Hale KJ, McCauley JP. An efficient new method for the desulfonylation of β-keto phenylsulfones. Tetrahedron Lett. 1989; 30: 5579-5582. doi: 10.1016/S0040-4039(01)93804-3
132. Harris AR, Mason TJ, Hannah GR A novel reductive desulphonation of acyl sulphones. J Chem Res. 1990; 218-219.
133. Pavlíčková L, Koutek B, Velek J, Souček M. Preparation of substituted acetophenones from carboxylic acid esters. Collect Czech Chem Commun. 1974; 39: 1216-1219. doi: 10.1135/cccc19741216
134. Liu Q, Han B, Liu Z, Yang L, Liu Z-L, Yu W. Photochemical reductive desulfonylation of β-ketosulfones by ascorbic acid. Tetrahedron Lett. 2006; 47: 1805-1807. doi: 10.1016/j.tetlet.2006.01.023
135. Allonas X, Lalevée J, Fouassier J. A new approach of the photoinitiator reactivity. J Photopolym Sci Technol. 2004; 17: 29-34. doi: 10.2494/photopolymer.17.29
136. Wu J-C, Gong L-B, Xia Y, Song R-J, Xie Y-X, Li J-H Nickel-catalyzed Kumada reaction of tosylalkanes with Grignard reagents to produce alkenes and modified arylketones. Angew Chem Int Ed. 2012; 51: 9909-9013.
137. Tanikaga R, Hosoya K, Kaji A. Synthesis of enantiomerically pure (4S)-2-alken-4-olides via (2S)-1-phenylsulfonyl-2-alkanols. Synthesis. 1987; 1987: 389-390. doi: 10.1055/s-1987-27956
138. Tanikaga R, Hosoya K, Kaji A. Synthesis of enantiomerically pure 2,5-disubstituted tetrahydrofurans using readily prepared (2S)-1- phenylsulphonylalkan-2-ols. J Chem Soc, Perkin Trans. 1987; 1: 1799-1803. doi: 10.1039/p19870001799
139. Bertus P, Phansavath P, Ratovelomanana-Vidal V, Genêt J-P, Touati A, Homri T, Hassine BB. Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts: synthesis of enantiomerically pure butenolides and γ -butyrolactones. Tetrahedron Asymm. 1999; 10: 1369-1380. doi: 10.1016/S0957-4166(99)00113-5
140. Sato T, Okumura Y, Itai J, Fujisawa T. (S)-β,ω -Dihydroxyalkyl phenyl sulfones. Synthesis by bakers yeast reduction and use as precursors of optically active lactones. Chem Lett. 1988; 17: 1537-1540.
141. Kozikowski AP, Mugrage BB, Li CS, Felder L. Chemistry of baker's yeast reduction products: use of optically active (S)-(+)-1-(p-toluenesulfonyl)propan- 2-ol and (S)-(+)-1-(phenylsulfonyl)propan-2-ol in synthesis. Tetrahedron Lett. 1986; 27: 4817-4820. doi: 10.1016/S0040-4039(00)85071-6
142. Tanikaga R, Hosoya K, Kaji A. Reactions of (2S)-1-arenesulfonyl-2-alkanol dianions with aldehydes, application to the synthesis of enantiomerically pure (3S)-1-alken-3-ols and (2E,4S)-4-hydroxy-2-alkenenitriles. Chem Lett. 1987; 16: 829-832. doi: 10.1246/cl.1987.829
143. Tanikaga R, Hosoya K, Kaji A. Unusual stereoselection in the reaction of dianions derived from 1-phenylsulphonylalkan-2-ols with electrophilic reagents. J Chem Soc, Perkin Trans. 1988; 1: 2397-2402. doi: 10.1039/p19880002397
144. Alvarez-Ibarra C, Cuervo-Rodríguez R, Fernández-Monreal MC, Ruiz MP. Synthesis and conformational study of β-hydroxy sulfones, bioisosteres of oxisuran metabolites, and their O-methyl derivatives. Tetrahedron. 1996; 52: 11239-11256. doi: 10.1016/0040-4020(96)00650-3
145. Csuk R, Glaenzer BI. Baker's yeast mediated transformations in organic chemistry. Chem Rev. 1991; 91: 49-97. doi: 10.1021/cr00001a004
146. Maguire AR, Lowney DG. Asymmetric reduction of 1-methylsulfonylalkan-2- ones with baker's yeast. J Chem Soc, Perkin Trans. 1997; 1: 235-238. doi: 10.1039/a605132d
147. Hiraoka C, Matsuda M, Suzuki Y, Fujieda S, Tomita M, Fuhshuku K, Obata R, Nishiyama S, Sugai T. Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones. Tetrahedron Asymm. 2006; 17: 3358-3367. doi: 10.1016/j.tetasy.2006.12.013
148. Gotor V, Rebolledo F, Liz R. Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata. Tetrahedron Asymm. 2001; 12: 513-515. doi: 10.1016/S0957-4166(01)00048-9
149. Cho BT, Kim DJ. Efficient synthesis of optically active β-hydroxy p-tolylsulfones with very high enantiomeric excess via CBS-oxazaborolidine- catalyzed borane reduction. Tetrahedron Asymm. 2001; 12: 2043-2047. doi: 10.1016/S0957-4166(01)00359-7
150. Wang G-Y, Liu X-Y, Zhao G Synthesis of dendrimer-supported prolinols and their application in enantioselective reduction of ketones. Synlett. 2006; 1150-1154.
151. Zhao G, Hu J, Qian Z, Yin W. Enantioselective reduction of β-keto sulfones using the NaBH 4/Me 3SiCl system catalyzed by polymer-supported chiral sulfonamide. Tetrahedron Asymm. 2002; 13: 2095-2098. doi: 10.1016/S0957-4166(02) 00546-3
152. Eagon S, Ball-Jones N, Haddenham D, Saavedra J, DeLieto C, Buckman M, Singaram B. Enantioselective reduction of -substituted ketones mediated by the boronate ester TarB-NO 2. Tetrahedron Lett. 2010; 51: 6418-6421. doi: 10.1016/j.tetlet.2010.09.146
153. Bertus P, Phansavath P, Ratovelomanana-Vidal V, Genêt J-P, Touati A, Homri T, Hassine BB. General synthesis of chiral β-hydroxy sulfones via enantioselective ruthenium-catalyzed hydrogenation. Tetrahedron Lett. 1999; 40: 3175-3178. doi: 10.1016/S0040-4039(99)00453-0
154. Zhang H-L, Hou X-L, Dai, L-X, Luo Z-B. Synthesis of a biferrocene diphosphine ligand with only planar chirality and its application in the Rh-catalyzed asymmetric hydrogenation of β-keto sulfones. Tetrahedron
155. Ding Z, Yang J, Wang T, Shen Z, Zhang Y. Dynamic kinetic resolution of β-keto sulfones via asymmetric transfer hydrogenation. Chem Commun. 2009; 571-573. doi: 10.1039/b818257d
156. Hamed EA, El-Saadi MSM, El-Hegazy FM. Novel route to β-chloro vinyl sulfones via the action of phosphorus pentachloride on phenacyl aryl sulfones in chloroform. Synth Commun. 1995; 25: 3471-3478. doi: 10.1080/00397919508013871
157. Paulvannan K, Stille JR. Heterocycle formation through aza-annulation: stereochemically controlled syntheses of (±)-5-epitashiromine and (±)-tashiromine. J Org Chem. 1994; 59: 1613-1620. doi: 10.1021/jo00086a009
158. Guravaiah N, Rao VR. Synthesis of a new class of sulfone-linked 3-([1,2,3]-thiadazol-4-yl)-chromen-2-ones. Phosphorus Sulfur Silicon Relat Elem. 2010; 185: 361-367. doi: 10.1080/10426500902797137
159. Guravaiah N, Rao VR. Simple strategy for sulfonyl ethynylogs of coumarins. Synth Commun. 2011; 41: 2693-2700. doi: 10.1080/00397911.2010.515344
160. Huang DF, Shen TY. A versatile total synthesis of epibatidine and analogs. Tetrahedron Lett. 1993; 34: 4477-4480. doi: 10.1016/0040-4039(93)88063- O
161. Jurášek A, Polakovičová D, Kováč J. Study of keto-enol tautomerism and alkylation reactions of β-ketosulphones of 5-nitrofuran series. Collect Czech Chem Commun. 1981; 46: 3115-3121. doi: 10.1135/cccc19813115
162. Toyohiko A, Satomi T, Kimio S, Takayuki S. New methods and reagents in organic synthesis. 46. Trimethylsilyldiazomethane: a convenient reagent for the O-methylation of phenols and enols. Chem Pharm Bull. 1984; 32: 3759-3760.
163. Kong HI, Crichton JE, Manthorpe JM. Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of -trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane. Tetrahedron Lett. 2011; 52: 3714-3717. doi: 10.1016/j.tetlet.2011.05.015
164. Pasetto P, Walczak MC. A Mitsunobu route to C-glycosides. Tetrahedron. 2009; 65: 8468-8477. doi: 10.1016/j.tet.2009.08.024
165. Giblin GMP, Simpkins NS. Addition-elimination reactions of β-oxygenated vinyl sulphones. J Chem Soc Chem Commun. 1987; 207-208. doi: 10.1039/c39870000207
166. Specklin S, Bertus P, Weibel J-M, Pale P. A versatile and highly stereoselective access to vinyl triflates derived from 1,3-dicarbonyl and related compounds. J Org Chem. 2008; 73: 7845-7848. doi: 10.1021/jo8015049
167. Plazuk D, Rybarczyk-Pirek A, Zakrzewski J. β-Ferrocenyl-,β- unsaturated phosphonates and sulfones. J Organomet Chem. 2004; 689: 1165-1171. doi: 10.1016/j.jorganchem.2003.12.044
168. Bernard AM, Frongia A, Piras PP, Secci F, Spiga M. Synthesis of enantiomerically enriched secondary and tertiary phenylthio- and phenoxy-aldols. Tetrahedron Lett. 2008; 49: 3037-3041. doi: 10.1016/j.tetlet.2008.03.066
169. Dichtl A, Seyfried M, Schoening K-U A novel method for the synthesis of n-alkoxyamines starting from nitroxide radicals and ketones. Synlett. 2008; 1877-1881.
170. Pokhodylo N, Matiychuk V, Obushak M. (Arylsulfonyl)acetones and -acetonitriles: new activated methylenic building blocks for synthesis of 1,2,3-triazoles. Synthesis. 2009; 2321-2323. doi: 10.1055/s-0029-1216850
171. Takikawa H, Hikita K, Suzuki K Synthesis of highly functionalized isoxazoles via base-promoted cyclocondensation of stable nitrile oxides with active methylene compounds. Synlett. 2007; 2252-2256.
172. Garrido JL, Alonso I, Carretero JC. One-step palladium-catalyzed synthesis of substituted dihydrofurans from the carbonate derivatives of γ -hydroxy-,β-unsaturated sulfones. J Org Chem. 1998; 63: 9406-9413. doi: 10.1021/jo981391r
173. Marco JL. Michael reactions of β-keto sulfoxides and β-keto sulfones. J Org Chem. 1997; 62: 6575-6581. doi: 10.1021/jo9705982
174. Kawai H, Sugita Y, Tokunaga E, Shibata N. Synthesis of isoxazole triflones. Eur J Org Chem. 2012; 1295-1298. doi: 10.1002/ejoc.201101814
175. Qian C-Y, Nishino H, Kurosawa K. Manganese(III)-mediated free-radical cyclization of acitve methylene compounds, alkenes and molecular oxygen. Syntheses of sulfur- and phosphorus-containing 1,2-dioxan-3-ols. J Heterocycl Chem. 1993; 30: 209-216. doi: 10.1002/jhet.5570300136
176. Arai S, Nakayama K, Suzuki Y, Hatano K, Shioiri T. Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions. Tetrahedron Lett. 1998; 39: 9739-9742. doi: 10.1016/S0040-4039(98)02239-4
177. Li C, Zhang Q, Tong X. Amine-catalyzed (3+n) annulations of 2-(acetoxymethyl)buta-2,3-dienoates with 1,n-bisnucleophiles (n = 3-5). Chem Commun. 2010; 46: 7828-7830. doi: 10.1039/c0cc01966f
178. Mizuyama N, Murakami Y, Nakatani T, Kuronita K, Kohra S, Ueda K, Hiraoka K, Tominaga Y. Reaction of 6-aryl- or styryl-4-methylsulfanyl-2-oxo-2H-pyrans with active methylene compounds and fluorescence properties of the products. J Heterocycl Chem. 2008; 45: 265-277. doi: 10.1002/jhet.5570450133
179. Atechian S, Nock N, Norcross RD, Ratni H, Thomas AW, Verron J, Masciadri R. New vistas in quinoline synthesis. Tetrahedron. 2007; 63: 2811-2823. doi: 10.1016/j.tet.2007.01.050
180. Peng C, Wang Y, Liu L, Wang H, Zhao J, Zhu Q. p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: efficient synthesis of 4-alkyl-2,3-disubstituted quinolines. Eur J Org Chem. 2010; 818-822. doi: 10.1002/ejoc.200901257
181. Gubin J, de Vogelaer H, Inion H, Houben C, Lucchetti J, Mahaux J, Rosseels G, Peiren M, Clinet M, Polster P. Novel heterocyclic analogues of the new potent class of calcium entry blockers: 1-[[4-(aminoalkoxy)phenyl] sulfonyl]indolizines. J Med Chem. 1993; 36: 1425-1433. doi: 10.1021/jm00062a015
182. Bunce RA, Rogers D, Nago T, Bryant SA. 4H-1-Benzopyrans by a tandem SN 2-SN Ar reaction. J Heterocycl Chem. 2008; 45: 547-550. doi: 10.1002/jhet.5570450238
183. Nakamura M, Yoshikai N, Toganoh M, Nakamura E. [3+3]cycloaddition reaction of dipolar trimethylenemethane with active methylene compound. Synlett. 2001; 1030-1033. doi: 10.1055/s-2001-14653
184. Kim B, Kim K. A facile and convenient synthesis of 3-alkylamino-5- arylthiophenes with a variety of substituents at C-2 and studies of reaction mechanisms. J Org Chem. 2000; 65: 3690-3699. doi: 10.1021/jo991884b
185. Simon C, Constantieux T, Rodriguez J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur J Org Chem. 2004; 4957-4980. doi: 10.1002/ejoc.200400511
186. Sherif S, Hussein A. Syntheses with heterocyclic β-enaminonitriles: an expeditious synthetic approach to polyfunctionally substituted 5-phenylsulfonylthiophenes and their fused derivatives. Monatsh Chem. 1997; 128: 687-696. doi: 10.1007/BF00807600
187. Abelman MM, Smith SC, James DR. Cyclic ketones and substituted -keto acids as alternative substrates for novel Biginelli-like scaffold syntheses. Tetrahedron Lett. 2003; 44: 4559-4562. doi: 10.1016/S0040-4039(03)00985-7
188. Gladkov ES, Chebanov VA, Desenko SM, Shishkin OV, Shishkina SV, Dallinger D, Kappe CO. Multicomponent cyclocondensations of β-Ketosulfones with aldehydes and aminoazole building blocks. Heterocycles. 2007; 73: 469-480. doi: 10.3987/COM-07-S(U)19
189. Brian T The reaction of aldehydes and ammonium acetate with some acetonyl and phenacyl derivatives: a correction. Synthesis. 1993; 755-757.
190. Pandiarajan K, Benny JCN. One step synthesis of 3,4-dihydro-2H-1,3- oxazines. J. Chem Soc Perkin Trans. 1992; 1: 2055-2056. doi: 10.1039/p19920002055
191. Shaaban MR, Saleh TS, Mayhoub AS, Farag AM. Single step synthesis of new fused pyrimidine derivatives and their evaluation as potent Aurora-A kinase inhibitors. Eur J Med Chem. 2011; 46: 3690-3695. doi: 10.1016/j.ejmech.2011.05. 033
192. Pang W, Xin Y, Zhu S, Jiang H, Zhu S. Unexpected formation of fluorine-containing tetrahydrocarbazole during the reaction of indole, paraformaldehyde, and fluorine-containing β-ketoesters. Tetrahedron. 2011; 67: 6334-6339. doi: 10.1016/j.tet.2011.06.007
193. Fan L, Adams AM, Polisar JG, Ganem B. Studies on the chemistry and reactivity of -substituted ketones in isonitrile-based multicomponent reactions. J Org Chem. 2008; 73: 9720-9726. doi: 10.1021/jo8019708
194. Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M, Ross G. Multicomponent reactions as a powerful tool for generic drug synthesis. Synthesis. 2008; 4007-4011. doi: 10.1055/s-0028-1083239
195. Du Y, Tian F, Han L, Zhu N. Three-component reaction of β -ketosulfone, formaldehyde, and thiol or thiophenol in water. Phosphorus Sulfur Silicon Relat Elem. 2012; 187: 1011-1016. doi: 10.1080/10426507.2012.657505
196. Kuninobu Y, Matsuzaki H, Nishi M, Takai K. Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones. Org Lett. 2011; 13: 2959-2961. doi: 10.1021/ol2008507
197. Zhang T, Huang X, Xue J, Sun S. Ring expansion reaction of -sulfonyl cyclic ketones via insertion of arynes into C-C: a facile and mild access to medium- and large-sized benzannulated carbocycles. Tetrahedron Lett. 2009; 50: 1290-1294. doi: 10.1016/j.tetlet.2009.01.001
198. Huang X, Xue J. A novel multicomponent reaction of arynes, β-keto sulfones, and Michael-type acceptors: a direct synthesis of polysubstituted naphthols and naphthalenes. J Org Chem. 2007; 72: 3965-3968. doi: 10.1021/jo070241q
199. Bin JK, Lee JS, Kim K. Potassium hydroxide-mediated novel rearrangement of 2-alkyl-sulfonyl-2-arylsulfonyl-1-phenylethanones to 1-aryl-2- (arylsulfonylmethanesulfonyl)ethanones. Org Lett. 2004; 6: 4297-4300. doi: 10.1021/ol0482285
200. Wolf WM. The fungicidal activity of β-keto sulfones. Molecular conformation of -phenylhydrazono-β-ketosulfones as determined by an X-ray analysis. J Mol Struct. 1999; 474: 113-124. doi: 10.1016/S0022-2860(98)00565-1