Comparative studies on conventional and ultrasound-assisted synthesis of novel homoallylic alcohol derivatives linked to sulfonyl dibenzene moiety in aqueous media

Journal of Chemistry

Volumn , Issue , 2013, Pages

  Mady, Mohamed F ^a,b   El Kateb, Ahmed A ^b   Zeid, Ibrahim F ^c   Jorgensen, Kåre B ^a  

^a UNIVERSITY OF STAVANGER   (Norway)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c Menoufia University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84866252509     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2013/364036     Document Type: Article

References (62)

1. Cravotto G., Cintas P., Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chemical Society Reviews 2006 35 2 180 196 10.1039/b503848k (Pubitemid 43485008)
2. Bang K., Lee K., Park Y. K., Lee P. H., Sonochemical Reformatsky reaction using indium. Bulletin of the Korean Chemical Society 2002 23 9 1272 1276 2-s2.0-0037145171
3. Lee P. H., Indium and gallium-mediated addition reactions. Bulletin of the Korean Chemical Society 2007 28 1 17 28 10.5012/bkcs.2007.28.1.017
4. Saleh T. S., Abd EL-Rahman N. M., Ultrasound promoted synthesis of substituted pyrazoles and isoxazoles containing sulphone moiety. Ultrasonics Sonochemistry 2009 16 2 237 242 2-s2.0-54149085525 10.1016/j.ultsonch.2008.07. 012
5. Mokhtar M., Saleh T. S., Ahmed N. S., Al-Thabaiti S. A., Al-Shareef R. A., An eco-friendly N-sulfonylation of amines using stable and reusable Zn-Al-hydrotalcite solid base catalyst under ultrasound irradiation. Ultrasonics Sonochemistry 2011 18 1 172 176 2-s2.0-77956424733 10.1016/j.ultsonch.2010.05. 001
6. Bian Y. J., Li J. T., Li T. S., Applications of ultrasound in organic synthesis using metal reagent. Chinese Journal of Organic Chemistry 2002 22 227
7. Yoo J., Oh K. E., Keum G., Kang S. B., Kim Y., Indium-mediated monoallylation of carbonyl compounds with allylic chlorides and bisallylation of 2-pyridyl carboxylates with allylic halides in aqueous media. Polyhedron 2000 19 5 549 551 2-s2.0-0034653149 10.1016/S0277-5387(99)00405-2
8. Park S. Y., Han H. J., Yoo B., Facile synthesis of β -ketoesters by indium-mediated reaction of acyl cyanides with ethyl bromoacetate under ultrasonication. Bulletin of the Korean Chemical Society 2005 26 6 878 879 2-s2.0-22744434401 (Pubitemid 41032403)
9. Soengas G. R., Studies on indium-mediated additions to lactones: synthesis of 2-deoxy-2-substituted-3-ulosonic acids. Tetrahedron: Asymmetry 2010 21 18 2249 2253 10.1016/j.tetasy.2010.07.011
10. Lindley J., Lorimer J. P., Mason T. J., Enhancement of an Ullmann coupling reaction induced by ultrasound. Ultrasonics 1986 24 5 292 293 2-s2.0-0000297349
11. Otzen T., Wempe E. G., Kunz B., Bartels R., Lehwark-Yvetot G., Hänsel W., Schaper K. J., Seydel J. K., Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans synthesis and biological activity of new 2,4-diaminopyrimidines and 4 ′ -substituted 4-aminodiphenyl sulfones. Journal of Medicinal Chemistry 2004 47 1 240 253 2-s2.0-0346731227 10.1021/jm030931w (Pubitemid 38040508)
12. Sun Z. Y., Botros E., Su A. D., Kim Y., Wang E., Baturay N. Z., Kwon C. H., Sulfoxide-containing aromatic nitrogen mustards as hypoxia-directed bioreductive cytotoxins. Journal of Medicinal Chemistry 2000 43 22 4160 4168 2-s2.0-0034597583 10.1021/jm9904957
13. Davies I. W., Marcoux J. F., Corley E. G., Journet M., Cai D. W., Palucki M., Wu J., Larsen R. D., Rossen K., Pye P. J., DiMichele L., Dormer P., Reider P. J., A practical synthesis of a COX-2-specific inhibitor. Journal of Organic Chemistry 2000 65 25 8415 8420 2-s2.0-0034670533 10.1021/jo000870z
14. McMahon J. B., Gulakowski R. J., Weislow O. S., Schultz R. J., Narayanan V. L., Clanton D. J., Pedemonte R., Wassmundt F. W., Buckheit R. W., Decker W. D., White E. L., Bader J. P., Boyd M. R., Diarylsulfones, a new chemical class of nonnucleoside antiviral inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrobial Agents and Chemotherapy 1993 37 4 754 760 2-s2.0-0027447592 (Pubitemid 23096874)
15. Neamati N., Mazumder A., Zhao H., Sunder S., Burke T. R., Schultz R. J., Pommier Y., Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors. Antimicrobial Agents and Chemotherapy 1997 41 2 385 393 2-s2.0-0031046693 (Pubitemid 27111035)
16. Doherty G. A., Kamenecka T., McCauley E., Van Riper G., Mumford R. A., Tong S., Hagmann W. K., N-aryl 2,6-dimethoxybiphenylalanine analogues as VLA-4 antagonists. Bioorganic and Medicinal Chemistry Letters 2002 12 5 729 731 2-s2.0-0037060923 10.1016/S0960-894X(02)00009-4 (Pubitemid 34164606)
17. Faucher A. M., White P. W., Brochu C., Grand-Maître C., Rancourt J., Fazal G., Discovery of small-molecule inhibitors of the ATPase activity of human papillomavirus E1 helicase. Journal of Medicinal Chemistry 2004 47 1 18 21 2-s2.0-0346731236 10.1021/jm034206x (Pubitemid 38040486)
18. Tomida M., Yamamoto-Yamaguchi Y., Hozumi M., Pregnancy associated increase in mRNA for soluble D-factor/LIF receptor in mouse liver. FEBS Letters 1993 334 2 193 197 2-s2.0-0027452011 10.1016/0014-5793(93)81710-H (Pubitemid 23330580)
19. Denmark S. E., Fu J., Catalytic enantioselective allylation with chiral Lewis bases. Chemical Communications 2003 2 167 170 10.1039/b208065f (Pubitemid 36138701)
20. Petrier C., Luche J. L., Allylzinc reagents additions in aqueous media. The Journal of Organic Chemistry 1985 50 6 910 912 10.1021/jo00206a047
21. Zha Z., Wang Y., Yang G., Zhang L., Wang Z., Efficient barbier reaction of carbonyl compounds improved by a phase transfer catalyst in water. Green Chemistry 2002 4 6 578 580 2-s2.0-0036920249 10.1039/b206452a
22. Basu M. K., Banik B. K., Samarium-mediated Barbier reaction of carbonyl compounds. Tetrahedron Letters 2001 42 2 187 189 2-s2.0-0035825077 10.1016/S0040-4039(00)01961-4 (Pubitemid 32332659)
23. Wang Z., Yuan S., Li C. J., Gallium-mediated allylation of carbonyl compounds in water. Tetrahedron Letters 2002 43 29 5097 5099 2-s2.0-0037100030 10.1016/S0040-4039(02)00995-4 (Pubitemid 34686875)
24. Li C. J., Chan T. H., Organometallic reactions in aqueous media with indium. Tetrahedron Letters 1991 32 48 7017 7020 2-s2.0-0026045466 10.1016/0040-4039(91)85028-4
25. Xu B., Hammond G. B., On the nature of organoindium intermediates: the formation of readily isolable difluoropropargylindium reagents and their regioselectivity towards electrophilic substitutions. Chemistry 2008 14 32 10029 10035 10.1002/chem.200801367
26. Kargbo R., Takahashi Y., Bhor S., Cook G. R., Lloyd-Jones G. C., Shepperson I. R., Readily accessible, modular, and tuneable BINOL 3, 3 ′-perfluoroalkylsulfones: highly efficient catalysts for enantioselective in-mediated imine allylation. Journal of the American Chemical Society 2007 129 13 3846 3847 2-s2.0-34247139301 10.1021/ja070742t (Pubitemid 46595505)
27. Tan K. L., Jacobsen E. N., Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst. Angewandte Chemie 2007 119 8 1337 1339 10.1002/ange.200603354
28. Haddad T. D., Hirayama L. C., Singaram B., Indium-mediated asymmetric barbier-type allylations: additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents. The Journal of Organic Chemistry 2010 75 3 642 649 10.1021/jo902173j
29. Cintas P., Palmisano G., Cravotto G., Power ultrasound in metal-assisted synthesis: from classical Barbier-like reactions to click chemistry. Ultrasonics Sonochemistry 2011 18 4 836 841 2-s2.0-79952448024 10.1016/j.ultsonch.2010.11. 020
30. Alcaide B., Almendros P., del Campo T. M., Highly stereoselective metal-mediated entry to functionalized tetrahydrothiophenes by barbier-type carbonyl-addition reactions. European Journal of Organic Chemistry 2008 2008 15 2628 2634 10.1002/ejoc.200800067
31. Kargbo R. B., Cook G. R., Stereoselective indium-mediated allylation reactions. Current Organic Chemistry 2007 11 15 1287 1309 10.2174/ 138527207782023139 (Pubitemid 47578197)
32. Yadav J. S., Subba Reddy B. V., Vishnumurthy P., Biswas S. K., Indium-mediated allylation/propargylation of α -diazoketones: a facile synthesis of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols. Tetrahedron Letters 2007 48 38 6641 6643 2-s2.0-34548018354 10.1016/j.tetlet.2007.07.136 (Pubitemid 47284251)
33. Loh T. P., Chau G. L., Discovery of indium complexes as water-tolerant Lewis acids. Chemical Communications 2006 26 2739 2749 10.1039/b600568n (Pubitemid 43962805)
34. Yamamoto Y., Asao N., Selective reactions using allylic metals. Chemical Reviews 1993 93 6 2207 2293 2-s2.0-4243893500
35. Reinhard W. H., Diastereogenic addition of crotylmetal compounds to aldehydes. Angewandte Chemie 1982 21 8 555 566 10.1002/anie.198205553
36. Yoshinori Y., Acyclic stereocontrol via allylic organometallic compounds. Accounts of Chemical Research 1987 20 7 243 249 10.1021/ar00139a002
37. Pae A. N., Cho Y. S., Indium-mediated organic reactions in aqueous media. Current Organic Chemistry 2002 6 8 715 737 10.2174/1385272023374030 (Pubitemid 34661740)
38. Podlech J., Maier T. C., Indium in organic synthesis. Synthesis 2003 5 633 655 2-s2.0-0037253161 (Pubitemid 36403453)
39. Li C. J., Chan T. H., Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999 55 37 11149 11176 2-s2.0-0033543497 10.1016/S0040-4020(99)00641-9 (Pubitemid 29400730)
40. Augé J., Lubin-Germain N., Uziel J., Recent advances in indium-promoted organic reactions. Synthesis 2007 12 1739 1764 2-s2.0-34347378107 10.1055/s-2007-983703 (Pubitemid 47020395)
41. Erian A. W., Sherif S. M., Gaber H. M., The chemistry of α -haloketones and their utility in heterocyclic synthesis. Molecules 2003 8 11 793 865 2-s2.0-3242790850 (Pubitemid 38982520)
42. Xian H., Pi J., A novel synthesis of sulfones via the 0.0-diethylphosphorotellurite ion-assisted coupling of arenesulfonyl chlorides with active halides. Synthetic Communications 1990 20 15 2291 2295 10.1080/00397919008053171
43. Xu C. L., Chen Z. C., Reaction of isopropylidene 5-tosyloxymalonate with alkyl halides- a new sulfur-oxygen scission of tosylate. Tetrahedron Letters 1991 32 25 2933 2934 2-s2.0-0025862933 10.1016/0040-4039(91)80653-N
44. Sunitha P., Kumar S., Rao B. R., Venkateshwarlu G., Microwave assisted efficient synthesis of β -keto-sulfones in aqueous medium. Green Chemistry Letters and Reviews 2008 1 3 179 183 10.1080/17518250802587873
45. Evano G., Blanchard N., Toumi M., Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chemical Reviews 2008 108 8 3054 3131 2-s2.0-51049095122 10.1021/cr8002505
46. Beletskaya I. P., Cheprakov A. V., Copper in cross-coupling reactions: the post-Ullmann chemistry. Coordination Chemistry Reviews 2004 248 2124 2337 2364 10.1016/j.ccr.2004.09.014
47. Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M., Aryl-Aryl bond formation one century after the discovery of the Ullmann reaction. Chemical Reviews 2002 102 5 1359 1470 10.1021/cr000664r (Pubitemid 35377647)
48. Zou J., Li F., Tao G. F., Microwave-assisted synthesis of diaryl or aryl-alkyl sulfones without catalyst. Chinese Chemical Letters 2009 20 1 17 20 10.1016/j.cclet.2008.10.017
49. Isaac M. B., Tak-Hang C., Indium mediated coupling of aldehydes with allyl bromides in aqueous media. The issue of regio- and diastereo-selectivity. Tetrahedron Letters 1995 36 49 8957 8960 2-s2.0-0028818170 10.1016/0040-4039(95) 01982-N
50. 2-mediated carbonyl allylation in fully aqueous media. Tetrahedron 2004 60 29 6129 6136 2-s2.0-3042555610 10.1016/j.tet.2004.05.046 (Pubitemid 38828298)
51. Sjoholm R., Rairama R., Ahonen M., Zinc mediated allylation of aldehydes and ketones with cinnamyl chloride in aqueous medium. Journal of the Chemical Society, Chemical Communications 1994 10 1217 1218 10.1039/c39940001217
52. Keltjens R., Vadivel S. K., De Gelder R., Klunder A. J. H., Zwanenburg B., Diastereoselective zinc-mediated Barbier-type allylation and propargylation of 3-formylcephalosporins. European Journal of Organic Chemistry 2003 9 1749 1758 2-s2.0-0037989840
53. Paquette L. A., Fundamental mechanistic characteristics and synthetic applications of allylations promoted by indium metal in aqueous media. Synthesis 2003 5 765 774 2-s2.0-0037246971 (Pubitemid 36403474)
54. Zimmerman H. E., Traxler M. D., The stereochemistry of the Ivanov and Reformatsky reactions. I. Journal of the American Chemical Society 1957 79 8 1920 1923 2-s2.0-33947468884
55. Abd EL-Rahman N. M., Saleh T. S., Mady M. F., Ultrasound assisted synthesis of some new 1,3,4-thiadiazole and bi(1,3,4-thiadiazole) derivatives incorporating pyrazolone moiety. Ultrasonics Sonochemistry 2009 16 1 70 74 2-s2.0-51449094400 10.1016/j.ultsonch.2008.05.001
56. Hill G. A., Kropa E. L., Some halogenated pinacolones. Journal of the American Chemical Society 1933 55 6 2509 2512 2-s2.0-33947343597
57. Ley S. V., Thomas A. W., Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation. Angewandte Chemie 2003 42 44 5400 5449 10.1002/anie.200300594 (Pubitemid 37466273)
58. Yoo E. J., Ahlquist M., Kim S. H., Bae I., Fokin V. V., Sharpless K. B., Chang S., Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: Controlling selectivity. Angewandte Chemie 2007 46 10 1730 1733 2-s2.0-34248146410 10.1002/anie.200604241 (Pubitemid 46981361)
59. Yoo E. J., Chang S., A new route to indolines by the Cu-catalyzed cyclization reaction of 2-ethynylanilines with sulfonyl azides. Organic Letters 2008 10 6 1163 1166 10.1021/ol800049b
60. Yasukawa T., Miyamura H., Kobayashi S., Copper-catalyzed, aerobic oxidative cross-coupling of alkynes with arylboronic acids: remarkable selectivity in 2,6-lutidine media. Organic & Biomolecular Chemistry 2011 9 6208 6210 10.1039/c1ob05915g
61. Kegelaers Y., Eulaerts O., Reisse J., Segebarth N., On the quantitative measure of a sonochemical effect in heterogeneous sonochemistry. European Journal of Organic Chemistry 2001 19 3683 3688 2-s2.0-0034799377 (Pubitemid 32963127)
62. Patel V. K., Sen D. J., Patel H. U., Patel C. N., Sonochemistry: The effect of sonic waves on chemical systems. Journal of Chemical and Pharmaceutical Research 2010 2 573