Studies with 1,3-diketones: A convenient synthesis of some tetrahydro-4H-benzopyran and tetrahydroquinoline derivatives

A facile, one-step synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-benzopyran derivatives 4a-e via cyclo-addition reactions of acrylonitrile derivatives 1a-e with 1,3-cyclohexandione 2 is described. On the other hand, the reactions of 2 with the thioamides 1f-h afforded 5-oxo-5,6,7,8-tetrahydroquinoline derivatives 9a-c in good yields. The structures of the prepared compounds were established from their elemental analyses, spectroscopic data, and by their chemical transformations. © 1996 John Wiley & Sons, Inc.