Heterocycles p. 1903 - 1921 (2010)
Update date:2022-09-26
Topics:
Kitabatake, Michikazu
Hashimoto, Aki
Saitoh, Toshiaki
Sano, Takehiro
Mohri, Kunihiko
Horiguchi, Yoshie
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. The Japan Institute of Heterocyclic Chemistry.
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