Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

Abstract

Imidazoheterocycles undergo efficient and regioselective sulfenylation with disulfides using the iodine/hydrogen peroxide system in ethanol at 25 °C. This green strategy tolerates a wide range of functional groups to afford diverse sulfenylated imidazoheterocycles in high yields. Moreover, the fipronil (a pesticide) skeleton can be readily attached to imidazoheterocycles using this strategy, which is significant in drug development.

Key words

iodine - sulfenylation - disulfide - imidazothiazole - imidazopyridine

• References

• 1a Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
• 1b Couty F, Evano G. Comprehensive Heterocyclic Chemistry . Elsevier; Oxford: 2008

Selected references, see:
• 2a Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Calonghi N, Cappadone C, Farruggia G, Zini M, Stefanelli C, Masotti L, Radin NS, Shoemaker RH. J. Med. Chem. 2008; 51: 809
• 2b Park J.-H, El-Gamal MI, Lee YS, Oh C.-H. Eur. J. Med. Chem. 2011; 46: 5769
• 2c Ali AR, El-Bendary ER, Ghaly MA, Shehata IA. Eur. J. Med. Chem. 2014; 75: 492
• 3a Vu CB, Bemis JE, Disch JS, Ng PY, Nunes JJ, Milne JC, Carney DP, Lynch AV, Smith JJ, Lavu S, Lambert PD, Gagne DJ, Jirousek MR, Schenk S, Olefsky JM, Perni RB. J. Med. Chem. 2009; 52: 1275
• 3b Ng PY, Bemis JE, Disch JS, Vu CB, Oalmann CJ, Lynch AV, Carney DP, Riera TV, Song J, Smith JJ, Lavu S, Tornblom A, Duncan M, Yeager M, Kriksciukaite K, Gupta A, Suri V, Elliot PJ, Milne JC, Nunes JJ, Jirousek MR, Vlasuk GP, Ellis JL, Perni RB. Lett. Drug Des. Discovery 2013; 10: 793
• 3c Matsuya Y, Kobayashi Y, Uchida S, Itoh Y, Sawada H, Suzuki T, Miyata N, Sugimoto K, Toyooka N. Bioorg. Med. Chem. Lett. 2013; 23: 4907
• 4 Andreani A, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Lannigan D, Smith J, Scudiero D, Kondapaka S, Shoemaker RH. Eur. J. Med. Chem. 2011; 46: 4311
• 5a Barradas JS, Errea MI, D’Accorso NB, Sepulveda CS, Damonte EB. Eur. J. Med. Chem. 2011; 46: 259
• 5b Juspin T, Laget M, Terme T, Azas N, Vanelle P. Eur. J. Med. Chem. 2010; 45: 840
• 6 Budriesi R, Ioan P, Leoni A, Pedemonte N, Locatelli A, Micucci M, Chiarini A, Galietta LJ. V. J. Med. Chem. 2011; 54: 3885
• 7a Belohlavek D, Malfertheiner PJ. Scand. J. Gastroenterol., Suppl. 1979; 54: 44
• 7b Boerner RJ, Moller HJ. Psychopharmakotherapie 1997; 4: 145
• 7c Abe Y, Kayakiri H, Satoh S, Inoue T, Sawada Y, Inamura N, Asano M, Aramori I, Hatori C, Sawai H, Oku T, Tanaka H. J. Med. Chem. 1998; 41: 4587
• 7d Mizushige K, Ueda T, Yukiiri K, Suzuki H. Cardiovasc. Drug. Rev. 2002; 20: 163
• 7e Okubo T, Yoshikawa R, Chaki S, Okuyama S, Nakazato A. Bioorg. Med. Chem. 2004; 12: 423
• 7f Mori H, Tanaka M, Kayasuga R, Masuda T, Ochi Y, Yamada H, Kishikawa K, Ito M, Nakamura T. Bone 2008; 43: 840

References for imidazo[2,1-b]thiazoles, see:
• 8a Kolavi G, Hegde V, Khazi IA. Tetrahedron Lett. 2006; 47: 2811
• 8b Huang G, Sun H, Qiu X, Jin C, Lin C, Shen Y, Jiang J, Wang L. Org. Lett. 2011; 13: 5224
• 8c Mukherjee C, Watanabe KT, Biehl ER. Tetrahedron Lett. 2012; 53: 6008

References for imidazo[1,2-a]pyridine, see:
• 9a Chernyak N, Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2743
• 9b Kianmehr E, Ghanbari M, Niri MN, Faramarzi R. J. Comb. Chem. 2010; 12: 41
• 9c Wang HG, Wang Y, Liang DD, Liu LY, Zhang JC, Zhu Q. Angew. Chem. Int. Ed. 2011; 50: 5678
• 9d Ma LJ, Wang XP, Yu W, Han B. Chem. Commun. 2011; 47: 11333
• 9e Albrecht Ł, Albrecht A, Ransborg LK, Jørgensen KA. Chem. Sci. 2011; 2: 1273
• 9f Sucunza D, Samadi A, Chioua M, Silva DB, Yunta C, Infantes L, Carreiras MC, Soriano E, Marco-Contelles J. Chem. Commun. 2011; 47: 5043
• 9g Yan RL, Yan H, Ma C, Ren ZY, Gao XA, Huang GS, Liang YM. J. Org. Chem. 2012; 77: 2024
• 9h Guchhait SK, Chandgude AL, Priyadarshani G. J. Org. Chem. 2012; 77: 4438
• 9i Nair DK, Mobin SM, Namboothiri IN. N. Org. Lett. 2012; 14: 4580
• 9j He C, Hao J, Xu H, Mo Y, Liu H, Han J, Lei A. Chem. Commun. 2012; 48: 11073
• 9k Zeng J, Tan YJ, Leow ML, Liu X.-W. Org. Lett. 2012; 14: 4386
• 9l Yan H, Yan R, Yang S, Gao X, Wang Y, Huang G, Liang Y. Chem. Asian J. 2012; 7: 2028
• 9m Hao Y, Sizhuo Y, Xiai G, Kang Z, Chao M, Rulong Y, Guosheng H. Synlett 2012; 23: 2961
• 9n Chioua M, Soriano E, Infantes L, Jimeno ML, Marco-Contelles J, Samadi A. Eur. J. Org. Chem. 2013; 35
• 9o Bagdi AK, Rahman M, Santra S, Majee A, Hajra A. Adv. Synth. Catal. 2013; 355: 1741
• 9p Gao Y, Yin M, Wu W, Huang H, Jiang H. Adv. Synth. Catal. 2013; 355: 2263
• 9q Mohan DC, Rao SN, Adimurthy S. J. Org. Chem. 2013; 78: 1266
• 9r Mohan DC, Donthiri RR, Rao SN, Adimurthy S. Adv. Synth. Catal. 2013; 355: 2217
• 9s Mohan DC, Sarang NB, Adimurthy S. Tetrahedron Lett. 2013; 54: 6077
• 9t Mohan DC, Rao SN, Ravi C, Adimurthy S. Asian J. Org. Chem. 2014; 3: 609
• 10a Mitchell SC, Nickson RM, Waring RH. Sulfur Rep. 1993; 13: 279
• 10b Kumagai H. Aroma Res. 2004; 5: 312
• 10c Legros J, Dehli JR, Bolm C. Adv. Synth. Catal. 2005; 347: 19
• 10d Konaklieva MI, Plotkin BJ. Recent Pat. Anti-Infect. Drug Discovery 2006; 1: 177
• 11a Raban M, Chern L.-J. J. Org. Chem. 1980; 45: 1688
• 11b Hamel P. J. Org. Chem. 2002; 67: 2854
• 12a Tudge M, Tamiya M, Savarin C, Humphrey GR. Org. Lett. 2006; 8: 565
• 12b Silveira CC, Mendes SR, Wolf L, Martins GM. Tetrahedron Lett. 2010; 51: 2014
• 12c Marcantoni E, Cipolletti R, Marsili L, Menichetti S, Properzi R, Viglianisi C. Eur. J. Org. Chem. 2013; 132
• 13 Jain S, Shukla K, Mukhopadhyay A, Suryawanshi SN, Bhakuni DS. Synth. Commun. 1990; 20: 1315
• 14a Maeda Y, Koyabu M, Nishimura T, Uemura S. J. Org. Chem. 2004; 69: 7688
• 14b Schlosser KM, Krasutsky AP, Hamilton HW, Reed JE, Sexton K. Org. Lett. 2004; 6: 819
• 14c Campbell JA, Broka CA, Gong L, Walker KA. M, Wang J.-H. Tetrahedron Lett. 2004; 45: 4073
• 14d Yadav JS, Reddy BV. S, Reddy YJ. Tetrahedron Lett. 2007; 48: 7034
• 14e Yadav JS, Reddy BV. S, Reddy YJ, Praneeth K. Synthesis 2009; 1520
• 15a Browder CC, Mitchell MO, Smith RL, el-Sulayman G. Tetrahedron Lett. 1993; 34: 6245
• 15b Fang X.-L, Tang R.-Y, Zhong P, Li J.-H. Synthesis 2009; 4183
• 15c Li Z, Hong J, Zhou X. Tetrahedron 2011; 67: 3690
• 15d Zou L.-H, Reball J, Mottweiler J, Bolm C. Chem. Commun. 2012; 48: 11307
• 15e La Regina G, Gatti V, Famiglini V, Piscitelli F, Silvestri R. ACS Comb. Sci. 2012; 14: 258
• 15f Ge W, Wei Y. Synthesis 2012; 44: 934
• 15g Ge W, Wei Y. Green Chem. 2012; 14: 2066
• 15h Sang P, Chen Z, Zou J, Zhang Y. Green Chem. 2013; 15: 2096
• 15i Azeredo JB, Godoi M, Martins GM, Silveira CC, Braga AL. J. Org. Chem. 2014; 79: 4125
• 16a Matsugi M, Murata K, Nambu H, Kita Y. Tetrahedron Lett. 2001; 42: 1077
• 16b Matsugi M, Murata K, Gotanda K, Nambu H, Anilkumar G, Matsumoto K, Kita Y. J. Org. Chem. 2001; 66: 2434
• 17 Wu Q, Zhao D, Qin X, Lan J, You J. Chem. Commun. 2011; 47: 9188
• 18 Yang F.-L, Tian S.-K. Angew. Chem. Int. Ed. 2013; 52: 4929
• 19a Hamdouchi C, de Blas J, Ezquerra J. Tetrahedron 1999; 55: 541
• 19b Ge W, Zhu X, Wei Y. Eur. J. Org. Chem. 2013; 6015
• 20a Hamdouchi C, Sanchez C, Ezquerra J. Synthesis 1998; 867
• 20b Patil SM, Kulkarni S, Mascarenhas M, Sharma R, Roopan SM, Roychowdhury A. Tetrahedron 2013; 69: 8255
• 20c Gao Z, Zhu X, Zhang R. RSC Adv. 2014; 4: 19891
• 20d Ravi C, Mohan DC, Adimurthy S. Org. Lett. 2014; 16: 2978
• 21 Hiebel M.-A, Berteina-Raboin S. Green Chem. 2014; in press; DOI: 10.1039/C4GC01462F
• 22 Tang R.-Y, Xie Y.-X, Xie Y.-L, Xiang J.-N, Li J.-H. Chem. Commun. 2011; 47: 12867
• 23a Sammelson RE, Caboni P, Durkin KA, Casida JE. Bioorg. Med. Chem. 2004; 12: 3345
• 23b Ozoe Y, Yagi K, Nakamura M, Akamatsu M, Miyake T, Matsumura F. Pestic. Biochem. Physiol. 2000; 66: 92
• 24 Disulfide 9 can be readily prepared according to the reported method, see: Clavel J.-L, Pelta I, Bars L, Charreau P. US 6,620,943, 2003
• 25a Cole LM, Nicholson RA, Casida JE. Pestic. Biochem. Physiol. 1993; 46: 47
• 25b Bertenshaw SR, Talley JJ, Rogier DJ, Graneto MJ, Koboldt CM, Zhang Y. Bioorg. Med. Chem. Lett. 1996; 6: 2827
• 26a Zhang C.-P, Wang ZL, Chen Q.-Y, Zhang C.-T, Gu Y.-C, Xiao JC. Angew. Chem. Int. Ed. 2011; 50: 1896
• 26b El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Lett. Org. Chem. 2012; 9: 118
• 27 Nobuta T, Hirashima S, Tada N, Miura T, Itoh A. Org. Lett. 2011; 13: 2576
• 28 Cressman HW. J, Thirt JR. J. Org. Chem. 1966; 31: 1279
• 29 Elliott AJ, Guzik H, Soler JR. J. Heterocycl. Chem. 1982; 19: 1437