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Paper | Regular issue | Vol 81, No. 8, 2010, pp.1903-1921
Published online, 25th June, 2010
DOI: 10.3987/COM-10-11992
An Efficient and Convenient Synthesis of 4,5,6,7-Tetrahydrothieno[3,2-c]pyridines by a Modified Pictet-Spengler Reaction via a Formyliminium Ion Intermediate

Michikazu Kitabatake, Aki Hashimoto, Toshiaki Saitoh, Takehiro Sano, Kunihiko Mohri, and Yoshie Horiguchi*

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4.