Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams

Abstract

N-Alkyl-N-allyl-2-bromobenzenesulfonamides were functionalized by selective E-cross-metathesis with various alkenes. Subsequent radical cyclization initiated by 2,2′-azobis(isobutyronitrile) and tris(trimethylsilyl)silane gave the corresponding 4-substituted benzosultams directly in moderate-to-good yields.

Key words

metathesis - cyclizations - radical reactions - sulfonamides - heterocycles

• References

• 1a Supuran CT, Casini A, Scozzafava A. Med. Res. Rev. 2003; 23: 535
• 1b Liu ZP, Takeuchi Y. Heterocycles 2009; 78: 1387
• 1c Wojciechowski K. Heterocycles 2002; 57: 1717
• 1d Liu ZP, Takeuchi Y. Heterocycles 2002; 56: 693
• 2 Wells GJ, Tao M, Josef KA, Bihovsky R. J. Med. Chem. 2001; 44: 3488
• 3 Chen X, Zhang S, Yang Y, Hussain S, He M, Gui D, Ma B, Jing C, Qiao Z, Zhu C, Yu Q. Bioorg. Med. Chem. 2011; 19: 7262
• 4 Zhang L, Wai JS, Embrey MW, Fisher TE, Egbertson MS, Payne LS, Guare JP. Jr, Vacca JP, Hazuda DJ, Felock PJ, Wolfe AL, Stillmock KA, Witmer MV, Moyer G, Schleif WA, Gabryelski LJ, Leonard YM, Lynch JJ. Jr, Michelson SR, Young SD. J. Med. Chem. 2003; 46: 453
• 5 Lombardino JG, Wiseman EH, McLamore W. J. Med. Chem. 1971; 14: 1171
• 6a Majumdar KC, Mondal S. Chem. Rev. 2012; 112: 7749
• 6b Bakker WI. I, Familoni OB, Padfield J, Snieckus V. Synlett 1997; 1079
• 6c Layman WJ. Jr, Greenwood TD, Downey AL, Wolfe JF. J. Org. Chem. 2005; 70: 9147
• 6d Norager NG, Juhl K. Synthesis 2010; 4273
• 6e Liu F, Musadji NY, Lecornué F, Jouannetaud M-P, Thibaudeau S. Tetrahedron 2010; 66: 7112
• 6f Enders D, Seppelt M. Synlett 2011; 402
• 7a Rolfe A, Young K, Hanson PR. Eur. J. Org. Chem. 2008; 5254
• 7b Rayabarapu DK, Zhou A, Jeon KO, Samarakoon T, Rolfe A, Siddiqui H, Hanson PR. Tetrahedron 2009; 65: 3180
• 7c Zang Q, Javed S, Porubsky P, Ullah F, Neuenswander B, Lushington GH, Basha FZ, Organ MG, Hanson PR. ACS Comb. Sci. 2012; 14: 211
• 8a Jiménez-Hopkins M, Hanson PR. Org. Lett. 2008; 10: 2223
• 8b Rolfe A, Samarakoon TB, Klimberg SV, Brzozowski M, Neuenswander B, Lushington GH, Hanson PR. J. Comb. Chem. 2010; 12: 850
• 8c Samarakoon TB, Loh JK, Rolfe A, Le LS, Yoon SY, Lushington GH, Hanson PR. Org. Lett. 2011; 13: 5148
• 8d Zang Q, Javed S, Hill D, Ullah F, Bi D, Porubsky P, Neuenswander B, Lushington GH, Santini C, Organ MG, Hanson PR. ACS Comb. Sci. 2012; 14: 456
• 9a Geoghegan K, Kelleher S, Evans P. J. Org. Chem. 2011; 76: 2187
• 9b Geoghegan K, Evans P, Rozas I, Alkorta I. Chem. Eur. J. 2012; 18: 13379
• 10 Rousseaux S, Gorelsky SI, Chung BK. W, Fagnou K. J. Am. Chem. Soc. 2010; 132: 10692
• 11a Ruppel JV, Kamble RM, Zhang XP. Org. Lett. 2007; 9: 4889
• 11b Miura T, Yamauchi M, Kosaka A, Murakami M. Angew. Chem. Int. Ed. 2010; 49: 4955
• 11c Pham MV, Ye B, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 10610
• 12a Zeng W, Chemler SR. J. Am. Chem. Soc. 2007; 129: 12948
• 12b Rambabu D, Murthy PV. N. S, Prasad KR. S, Kandale A, Deora GS, Rao MV. B, Pal M. Tetrahedron Lett. 2012; 53: 6577
• 13 Liu X-Y, Li C-H, Che C-M. Org. Lett. 2006; 8: 2707
• 14 Majumdar KC, Basu PK, Chattopadhyay SK. Tetrahedron 2007; 63: 793
• 15 Rowlands GJ. Tetrahedron 2010; 66: 1593
• 16 Preston AJ, Gallucci JC, Paquette LA. J. Org. Chem. 2006; 71: 6573
• 17 McReynolds MD, Dougherty JM, Hanson PR. Chem. Rev. 2004; 104: 2239
• 18 Kotha S, Dipak MK. Tetrahedron 2012; 68: 397
• 19 Alcaide B, Almendros P, Luna A. Chem. Rev. 2009; 109: 3817
• 20a Chen Q, Huo X, Zheng H, She X. Synlett 2012; 1349
• 20b Wang CH, White AR, Schwartz SN, Alluri S, Cattabiani TM, Zhang KK, Chan TM, Buevich AV, Ganguly AK. Tetrahedron 2012; 68: 9750
• 20c Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E. Angew. Chem. Int. Ed. 2009; 48: 2364
• 20d Bennasar M-L, Roca T, García-Díaz D. Synlett 2008; 1487
• 20e Edlin CD, Faulkner J, Fengas D, Helliwell M, Knight CK, House D, Parker J, Preece I, Quayle P, Raftery J, Richards SN. J. Organomet. Chem. 2006; 691: 5375
• 20f Seigal BA, Fajardo C, Snapper ML. J. Am. Chem. Soc. 2005; 127: 16329
• 20g Schmidt B, Pohler M. J. Organomet. Chem. 2005; 690: 5552
• 20h Dalgard JE, Rychnovsky SD. Org. Lett. 2004; 6: 2713
• 20i Clive DL. J, Yu M. Chem. Commun. (Cambridge) 2002; 2380
• 20j Cossy J, Pévet I, Meyer C. Eur. J. Org. Chem. 2001; 2841
• 20k Evans PA, Robinson JE, Moffett KK. Org. Lett. 2001; 3: 3269
• 20l Clive DL. J, Cheng H. Chem. Commun. (Cambridge) 2001; 605
• 21 Bressy C, Menant C, Piva O. Synlett 2005; 577
• 22 Baldwin JE. J. Chem. Soc., Chem. Commun. 1976; 734
• 23 Biswas D, Samp L, Ganguly AK. Tetrahedron Lett. 2010; 51: 2681
• 24 Evans P, McCabe T, Morgan BS, Reau S. Org. Lett. 2005; 7: 43
• 25 Chatgilialoglu C, Lalevée J. Molecules 2012; 17: 527
• 26a Cochet T, Roche D, Bellosta V, Cossy J. Eur. J. Org. Chem. 2012; 801
• 26b Cros F, Pelotier B, Piva O. Synthesis 2010; 233
• 26c Bakhrou N, Lamaty F, Martinez J, Colacino E. Tetrahedron Lett. 2010; 51: 3935
• 26d Dallinger D, Irfan M, Suljanovic A, Kappe CO. J. Org. Chem. 2010; 75: 5279
• 26e Coquerel Y, Rodriguez J. Eur. J. Org. Chem. 2008; 1125
• 27 Cardillo G, Orena M, Penna M, Sandri S, Tomasini C. Tetrahedron 1991; 47: 2263