Synthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions

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

heterocycles - cycloadditions - nitrile oxides - nitrile imines­ - Staudinger reactions

• 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