Synthesis, Table of Contents Synthesis 2012; 44(22): 3447-3452DOI: 10.1055/s-0032-1316794 paper © Georg Thieme Verlag Stuttgart · New YorkSynthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions Mátyás Milen* a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary b EGIS Pharmaceuticals PLC, Division for Chemical Research, P.O.B. 100, 1475 Budapest, Hungary Fax: +36(1)4633648 Email: gkeglevich@mail.bme.hu , Péter Ábrányi-Balogh a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary , András Dancsó b EGIS Pharmaceuticals PLC, Division for Chemical Research, P.O.B. 100, 1475 Budapest, Hungary Fax: +36(1)4633648 Email: gkeglevich@mail.bme.hu , György Keglevich* a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract The reaction of 6,7-dihydrothieno[3,2-c]pyridine derivatives with 1,3-dipoles, such as a nitrile oxides or nitrile imines, gave novel fused heterocycles. The Staudinger reaction of the starting material was also studied. This reaction was stereoselective and exclusively gave racemic cis-cycloadducts in which the thienopyridine core was fused with a β-lactam ring. Key words Key wordsheterocycles - cycloadditions - nitrile oxides - nitrile imines - Staudinger reactions Full Text References References 1a Quinn MJ, Fitzgerald DJ. Circulation 1999; 100: 1667 1b CAPRIE Steering Committee. Lancet. 1996 348. 1329 1c Sabatine MS. Eur. Heart. J. Suppl. 2006; 8: G31 1d Aalla S, Gilla G, Metil DS, Anumula RR, Vummenthala PR, Padi PR. Org. Process Res. Dev. 2012; 16: 240 1e Aradi D, Rideg O, Vorobcsuk A, Magyarlaki T, Magyari B, Kónyi A, Pintér T, Horváth IG, Komócsi A. Eur. J. Clinic. Invest. 2012; 42: 384 2a van der Meijden MW, Leeman M, Gelens E, Noorduin WL, Meekes H, van Enckevort WJ. P, Kaptein B, Vlieg E, Kellogg RM. Org. Process Res. Dev. 2009; 13: 1195 2b Aw D, Sharma JC. Postgrad. Med. J. 2012; 88: 34 2c Meves SH, Overbeck U, Endres HG, Krogias C, Neubauer H. Thromb. Haemostasis 2012; 107: 69 3 Aillaud I, Haurena C, Le Gall E, Martens T, Ricci G. Molecules 2010; 15: 8144 4a Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863 4b Coldham I, Hufton R. Chem. Rev. 2005; 105: 2765 4c Boger DL, Choi Y, Ishikawa H, Velicky J, Elliott GI. Org. Lett. 2005; 7: 4539 5a Grundmann C. Synthesis 1970; 344 5b Ferwanah A.-RS, Awadallah AD. Molecules 2005; 10: 492 6 Liu K.-Ch, Shelton BR, Howe RK. J. Org. Chem. 1980; 45: 3916 7 Mukaiyama T, Hoshino T. J. Am. Chem. Soc. 1960; 82: 5339 8 Minakata S, Okumura S, Nagamachi T, Takeda Y. Org. Lett. 2011; 13: 2966 9 Muri D, Bode JW, Carreira EM. Org. Lett. 2000; 2: 539 10a Shawali AS. Heterocycles 1983; 20: 2239 10b Shawali AS. Chem. Rev. 1993; 93: 2731 11a Staudinger M. Justus Liebigs Ann. Chem. 1907; 356: 51 11b France S, Guerin DJ, Miller SJ, Lectka T. Chem. Rev. 2003; 103: 2985 11c Jiao L, Liang Y, Xu J. J. Am. Chem. Soc. 2006; 128: 6060 12a Mehta PD, Sengar NP. S, Pathak AK. Eur. J. Med. Chem. 2010; 45: 5541 12b Fodor L, Csomós P, Csámpai A, Sohár P. Tetrahedron Lett. 2010; 51: 3205 12c Jiang J.-A, Zhai J.-J, Yu X.-H, Teng X, Ji Y.-F. Synthesis 2012; 44: 207 13a Milen M, Ábrányi-Balogh P, Dancsó A, Simig Gy, Keglevich Gy. Lett. Org. Chem. 2010; 7: 377 13b Milen M, Ábrányi-Balogh P, Mucsi Z, Dancsó A, Körtvélyesi T, Keglevich Gy. Curr. Org. Chem. 2011; 15: 1811 For the synthesis of 4-methyl-6,7-dihydrothieno[3,2-c]pyridine, see: 14a Dressler ML, Joullié MM. J. Het. Chem. 1970; 7: 1257 For the synthesis of 4-cyclohexyl-6,7-dihydrothieno[3,2-c]pyridine, see: 14b Madsen P, Lundbeck JM, Jakobsen P, Varming AR, Westergaard N. Bioorg. Med. Chem. 2000; 8: 2277 For the synthesis of 4-phenyl-6,7-dihydrothieno[3,2-c]pyridine, see: 14c Bremner JB, Browne EJ, Davies PE. Aust. J. Chem. 1980; 33: 1335 15a Miao W.-S, Xiong F, Wang M.-X, Huang Z.-T. Synth. Commun. 2000; 30: 3255 15b Abdallah TA. Synth. Commun. 2002; 32: 2459 16 Milen M, Ábrányi-Balogh P, Mucsi Z, Dancsó A, Frigyes D, Pongó L, Keglevich Gy. Curr. Org. Chem. in press 17 Rowe JE, Hegarty AF. J. Org. Chem. 1984; 49: 3038 18 Peifer C, Kinkel K, Abadleh M, Schollmeyer D, Laufer S. J. Med. Chem. 2007; 50: 1213 19 Chandramouli; Udupi RH, Bindu VH. Orient. J. Chem. 2007; 23: 1077
