Preparation of new nitrogen-bridged heterocycles. XXXIII. A new preparative method for thieno[3,2-α]indolizines

Article abstract of DOI:10.1248/cpb.41.1753

The treatment of 2-iminothieno[3,2-α]indolizine derivatives with potassium tert-butoxide generated exclusively potassium 1-(2- cyanovinyl)indolizine-2-thiolates through the ring opening of the initially formed thiin-2-imide ions. These 2-indolizinethiolates reacted with various alkylating agents to give the corresponding S-alkylated 1-vinylindolizine derivatives, and 2-acetonylthio- and 2-phenacylthio-1-(2- cyanovinyl)indolizines of these products smoothly underwent intramolecular Michael addition under the conditions employed here to afford the corresponding 2-acetyl- and 2-aroylthieno[3,2-α]indolizines in high yields with the elimination of a methylene compound.

Full text of DOI:10.1248/cpb.41.1753

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