A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol

Molecular Diversity

Volumn 14, Issue 3, 2010, Pages 533-541

  Rozentsveig, Igor B ^a   Popov, Aleksandr V ^a   Rozentsveig, Gulnur N ^a   Serykh, Valeriy Yu ^a   Chernyshev, Kirill A ^a   Krivdin, Leonid B ^a   Levkovskaya, Galina G ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

1,4 Oxathianes; Aziridines; Cascade reactions; Chloroimines; Imidoylchlorides; Ketones; Sulfonamides

Indexed keywords

1 (4 CHLOROBENZENE)SULFONAMIDO 2 (4 METHOXYPHENYL) 1 PHENYL 2 CHLOROETHENE; 2 (4 METHOXYPHENYL) 1 PHENYLETHANE 1 ON; AZIRIDINE DERIVATIVE; MERCAPTOETHANOL; N(3 PHENYL 1,4 OXATHIANE 2 YL)BENZENESULFONAMIDE; N[(4 CHLOROPHENYL)SULFONYL] 2 (1 NAPHTHYL)ACETAMIDE; N[(4 CHLOROPHENYL)SULFONYL] 2 (4 CHLOROPHENYL)ACETAMIDE; N[(4 CHLOROPHENYL)SULFONYL] 2 (4 METHOXYPHENYL)ACETAMIDE; N[(4 CHLOROPHENYL)SULFONYL] 2 (4 METHYLPHENYL)ACETAMIDE; N[3 (4 METHOXYPHENYL) 1,4 OXATHIANE 2 YL] 4 CHLOROBENZENESULFONAMIDE; N[3 (4 METHYLPHENYL) 1,4 OXATHIANE 2 YL] 4 CHLOROBENZENESULFONAMIDE; N[3 (5 CHLORO 2 THIENYL) 1,4 OXATHIANE 2 YL] 4 CHLOROBENZENESULFONAMIDE; PHENYLACETYLENE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; HYDROLYSIS; ISOMERIZATION; PRIORITY JOURNAL; REDUCTION; SUBSTITUTION REACTION; SYNTHESIS;

AMIDES; AZIRIDINES; CHEMISTRY, ORGANIC; DIOXANES; HETEROCYCLIC COMPOUNDS, 1-RING; MERCAPTOETHANOL; MOLECULAR CONFORMATION; STEREOISOMERISM; SULFONAMIDES;

EID: 78650169530     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-010-9231-z     Document Type: Article

References (45)

1. Hansch C, Sammes PG, Taylor JB (1990) Comprehensive medicinal chemistry, vol 2, Chapter 7.1. Pergamon Press, Oxford
2. EE Connor 1998 Sulfonamide antibiotics Prim Care Updat OB/GYNS 5 32 35 10.1016/S1068-607X(97)00121-2 10.1016/S1068-607X(97)00121-2 (Pubitemid 28071372)
3. Kleemann A, Engel J, Kutscher B, Reichert D (1999) Pharmaceutical substances, syntheses, patents, applications. 2nd ed. Stuggart Guide, Oxford Press, Thieme
4. BL Wilkinson LF Bornaghi TA Houston A Innocenti C Vullo CT Supuran SA Poulsen 2007 Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides J Med Chem 50 1651 1657 10.1021/jm061320h 1:CAS:528:DC%2BD2sXisFeit78%3D 10.1021/jm061320h 17343373 (Pubitemid 46564385)
5. C Almansa J Bartrolí J Belloc FL Cavalcanti R Ferrando LA Gómez I Ramis E Carceller M Merlos J García-Rafanell 2004 New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs J Med Chem 47 5579 5582 10.1021/jm040844j 1:CAS:528:DC%2BD2cXnvVahtr0%3D 10.1021/jm040844j 15481993 (Pubitemid 39382804)
6. W Chu J Rothfuss A d'Avignon C Zeng D Zhou RS Hotchkiss RH Mach 2007 Isatin sulfonamide analogs containing a michael addition acceptor: a new class of caspase 3/7 inhibitors J Med Chem 50 3751 3755 10.1021/jm070506t 1:CAS:528:DC%2BD2sXmslyqs70%3D 10.1021/jm070506t 17585855 (Pubitemid 47195482)
7. A Gopalsamy M Shi B Stauffer R Bahat J Billiard H Ponce-de-Leon L Seestaller-Wehr S Fukayama A Mangine R Moran G Krishnamurthy P Bodine 2008 Identification of diarylsulfone sulfonamides as secreted frizzled related protein-1 (sFRP-1) inhibitors J Med Chem 51 7670 7672 10.1021/jm801069w 1:CAS:528:DC%2BD1cXhsVOjsLzO 10.1021/jm801069w 19053830
8. MH Yates NJ Kallman CP Ley JN Wei 2009 Development of an acyl sulfonamide anti-proliferative agent, LY573636.Na Org Process Res Dev 13 255 262 10.1021/op800210x 1:CAS:528:DC%2BD1MXksVyqtA%3D%3D 10.1021/op800210x
9. Cloudsdale IS, Anderson RJ, Chinn HR, Craig GW, Deng L, Herberich-Patton PN, Pomes JC (1995) Herbicidal sulfonylamides. In: Baker DR, Basarab GS, Fenyes JG (eds) Synthesis and chemistry of agrochemicals IV. ACS, Washington, DC, pp 37-45
10. O Lukin V Gramlich R Kandre I Zhun T Felder CA Schalley G Dolgonos 2008 Designer dendrimers: branched oligosulfonimides with controllable molecular architectures J Am Chem Soc 128 8964 8974 10.1021/ja061606b 10.1021/ja061606b
11. Cremlyn R (1996) An introduction to organosulfur chemistry. Wiley, New York, pp 224-225
12. H Matsunaga T Ishizuka T Kunieda 2005 Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex Tetrahedron Lett 46 3645 3648 10.1016/j.tetlet.2005. 03.165 1:CAS:528:DC%2BD2MXjs1Sgu70%3D 10.1016/j.tetlet.2005.03.165 (Pubitemid 40591571)
13. Z Xu R Wang J Xu C Da W Yan C Chen 2003 Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by β-sulfonamide alcohol-titanium complex Angew Chem Int Ed 42 5747 5749 10.1002/anie.200352572 1:CAS:528:DC%2BD3sXpvFahtrw%3D 10.1002/anie.200352572 (Pubitemid 37522568)
14. TYH Wu S Ding NS Gray PG Schultz 2001 Solid-phase synthesis of 2,3,5-trisubstituted indoles Org Lett 3 3827 3830 10.1021/ol016525t 1:CAS:528:DC%2BD3MXnvVOiu7o%3D 10.1021/ol016525t 11720546 (Pubitemid 33625477)
15. D Crich AA Bowers 2007 Cyclic thioanhydrides: Linchpins for multicomponent coupling reactions based on the reaction of thioacids with electron-deficient sulfonamides and azides Org Lett 9 5323 5325 10.1021/ol702570x 1:CAS:528:DC%2BD2sXht1Kitr%2FE 10.1021/ol702570x 17979281
16. Greene TW, Wuts PGM (2007) Protective groups in organic synthesis. 4th ed. Wiley, New York, pp 224-225
17. J Bouffard Y Kim TM Swager R Weissleder SA Hilderbrand 2008 A highly selective fluorescent probe for thiol bioimaging Org Lett 10 37 40 10.1021/ol702539v 1:CAS:528:DC%2BD2sXhtl2itLjL 10.1021/ol702539v 18062694
18. VM Petrov GV Girichev H Oberhammer VN Petrova NI Giricheva AV Bardina SN Ivanov 2008 Molecular structure and conformations of para-methylbenzene sulfonamide and ortho-methylbenzene sulfonamide: gas electron diffraction and quantum chemical calculations study J Phys Chem A 112 2969 2976 10.1021/jp710532z 1:CAS:528:DC%2BD1cXitl2ltr4%3D 10.1021/jp710532z 18302350
19. SP Gupta 2007 Quantitative structure-activity relationship studies on zinc-containing metalloproteinase inhibitors Chem Rev 107 3042 3087 10.1021/cr030448t 1:CAS:528:DC%2BD2sXns1Clur8%3D 10.1021/cr030448t 17622180 (Pubitemid 47162904)
20. L De Luca G Giacomelli 2008 An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids J Org Chem 73 3967 3969 10.1021/jo800424g 1:CAS:528:DC%2BD1cXktlCiurk%3D 10.1021/jo800424g 18393527 (Pubitemid 351671478)
21. AR Katritzky V Rodriguez-Garcia SK Nair 2004 A general and efficient synthesis of sulfonylbenzotriazoles from N-chlorobenzotriazole and sulfinic acid salts J Org Chem 69 1849 1852 10.1021/jo035515y 1:CAS:528:DC%2BD2cXht12gt78%3D 10.1021/jo035515y 15058928 (Pubitemid 38366648)
22. S Caddick JD Wilden HD Bush SN Wadman DN Judd 2002 A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis Org Lett 4 2549 2551 10.1021/ol026181m 1:CAS:528:DC%2BD38XkslOisbw%3D 10.1021/ol026181m 12123373
23. R Bhuyan KM Nicholas 2007 Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T Org Lett 9 3957 3959 10.1021/ol701544z 1:CAS:528:DC%2BD2sXpsVKnsbs%3D 10.1021/ol701544z 17718576
24. VI/V Reduction Potentials J Am Chem Soc 127 16629 16640 10.1021/ja0542789 1:CAS:528: DC%2BD2MXhtFKlur%2FK 10.1021/ja0542789 16305252 (Pubitemid 41740414)
25. Espino CG, Du Bois J (2005) Rhodium(II)-catalyzed oxidative amination. In: Evans PA (eds) Modern rhodium-catalyzed organic reactions. Wiley-VCH, Weinheim, p 379
26. GG Levkovskaya TI Drozdova IB Rozentsveig AN Mirskova 1999 N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones Russ Chem Rev 68 581 604 10.1070/RC1999v068n07ABEH000476 1:CAS:528:DyaK1MXmtFKltb8%3D 10.1070/RC1999v068n07ABEH000476
27. R Bloch 1998 Additions of organometallic reagents to C=N bonds: reactivity and selectivity Chem Rev 98 1407 1438 10.1021/cr940474e 1:CAS:528:DyaK1cXjtlygtL4%3D 10.1021/cr940474e 11848938
28. L Zani S Alesi PG Cozzi C Bolm 2006 Dimethylzinc-mediated alkynylation of imines J Org Chem 71 1558 1562 10.1021/jo052273o 1:CAS:528: DC%2BD28Xlt1OlsQ%3D%3D 10.1021/jo052273o 16468805
29. IB Rozentsveig GG Levkovskaya AI Albanov AN Mirskova 2000 Reaction of N-(2,2,2-trichloroethylidene)arenesulfonamides with aromatic and heterocyclic compounds Russ J Org Chem 36 671 673 1:CAS:528:DC%2BD3cXnslWnur4%3D
30. IB Rozentsveig IT Evstaf'eva GG Levkovskaya AN Mirskova AI Albanov 2000 1,1-Bis(arylsulfonamido)-2,2-dichloroethanes and N-(1-hydroxy-2,2-dichloroethyl) arenesulfonamides in reactions of C-amidoalkylation of aromatic compounds Russ J Org Chem 36 813 815 1:CAS:528:DC%2BD3MXitVemtA%3D%3D
31. GN Rozentsveig IB Rozentsveig GG Levkovskaya IT Evstaf'eva AN Mirskova 2001 Reactions of N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides with aromatic and heterocyclic compounds Russ J Org Chem 37 1297 1301 10.1023/A:1013135722293 1:CAS:528:DC%2BD38XhtVamsLk%3D 10.1023/A:1013135722293 (Pubitemid 33382005)
32. TI Drozdova AN Mirskova 1998 Chemical transformations of N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides Russ J Org Chem 34 948
33. IB Rozentsveig GG Levkovskaya AN Mirskova TV Kashik 2000 Trichloroethylamides of arensulfonic acids under hydrolysis conditions Russ J Org Chem 36 1760 1764 1:CAS:528:DC%2BD3MXktVWjsbc%3D
34. IB Rozentsveig GG Levkovskaya GN Rozentsveig AN Mirskova LB Krivdin LI Larina AI Albanov 2005 Amidine derivatives of α-arylglycines from N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids and secondary amines Tetrahedron Lett 46 8889 8893 10.1016/j.tetlet.2005.10.079 1:CAS:528:DC%2BD2MXht1CisbnK 10.1016/j.tetlet.2005.10.079 (Pubitemid 41670524)
35. Rozentsveig IB, Popov AV, Rozentsveig GN, Chernyshev KA, Levkovskaya GG (2008) The reaction of N-(1-aryl-2,2,2-trichloroethyl)arensulfonamides with thioamides: a way to 5-arensulfonamido-4-aryl-1,3-thiatholes. Chem Heterocycl Comp 1587-1590
36. IB Rozentsveig AV Popov AV Brikov KA Chernyshev AN Mirskova GG Levkovskaya 2007 Reaction of 4-chloro-N-[2,2,2-trichloro-1-(4-methylphenyl) ethyl]benzenesulfonamide with diaza-18-crown-6 Russ J Org Chem 43 926 927 10.1134/s107042800706022x 1:CAS:528:DC%2BD2sXnslSns70%3D 10.1134/ S107042800706022X
37. IB Rozentsveig GN Rozentsveig AN Mirskova KA Chernyshev LB Krivdin GG Levkovskaya 2008 N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides in reactions with secondary amines Russ J Gen Chem 78 1135 1143 10.1134/s1070363208070141 10.1134/S1070363208070141
38. IB Rozentsveig AV Popov AN Mirskova GG Levkovskaya 2007 Unexpected transformations of arenesulfonic acids N-(1-aryl-2,2,2-trichloroethyl)amides in the presence of alkylthiols Russ J Org Chem 43 1559 1560 10.1134/ S1070428007100260 1:CAS:528:DC%2BD2sXhtlWgu77N 10.1134/S1070428007100260
39. GN Rozentsveig IB Rozentsveig GG Levkovskaya AN Mirskova 2003 Arylsulfonylaziridines and arylsulfonylaminoethenes from N-(1-Aryl-2,2-dichloro- 2-phenylethyl)arenesulfonamides Russ J Org Chem 39 1801 1802 10.1023/B:RUJO.0000019749.34777.6f 1:CAS:528:DC%2BD2cXitVygu7s%3D 10.1023/B:RUJO.0000019749.34777.6f (Pubitemid 39012419)
40. WB Smith BA Shoulders 1965 The nuclear magnetic resonance spectra of some 1,4-diheterocyclohexanes J Phys Chem 69 579 582 10.1021/j100886a036 1:CAS:528:DyaF2MXktFaltA%3D%3D 10.1021/j100886a036
41. C-H NMR coupling constants in cyclohexane, six-membered heterocycles and cyclohexanone derivatives J Am Chem Soc 124 13088 13096 10.1021/ja020317u 1:CAS:528:DC%2BD38XnvV2lsbY%3D 10.1021/ja020317u 12405836 (Pubitemid 35247121)
42. LJJ Hronowski Szarek WA 1982 Synthesis and biological evaluation of novel pyrimidine nucleoside analogs of 1,4-oxathiane, 1,4-dithiane, and 1,4-dioxane J Med Chem 25 522 526 10.1021/jm00347a008 1:CAS:528:DyaL38Xhs1eisr4%3D 10.1021/jm00347a008 7086837 (Pubitemid 12051975)
43. M Ioannoua MJ Porter F Saez 2005 Conversion of 1,3-oxathiolanes to 1,4-oxathianes using a silylated diazoester Tetrahedron 61 43 50 10.1016/j.tet.2004.10.063 10.1016/j.tet.2004.10.063 (Pubitemid 39573401)
44. Y Mizobe M Miyata I Hisaki Y Hasegawa N Tohnai 2006 Anomalous anthracene arrangement and rare excimer emission in the solid state: transcription and translation of molecular information Org Lett 8 4295 4298 10.1021/ol0616440 1:CAS:528:DC%2BD28XosVChtbY%3D 10.1021/ol0616440 16956210 (Pubitemid 44449965)
45. JC Chapman RG Sherman 2000 Restricted motion of guests confined in carceplexes and capsules J Org Chem 65 513 516 10.1021/jo991433r 1:CAS:528:DyaK1MXnslSlu7o%3D 10.1021/jo991433r 10813965 (Pubitemid 30061136)