STEREOCHEMISTRY OF ELECTROPHILIC ANNELATION OF 2-ALLYL- (AND 2-CYCLOHEXEN-1-YL)THIO-1,5-NAPHTHYRIDINES TO THIAZOLO-1,5-NAPHTHYRIDINIUM SALTS

Article abstract of DOI:10.1007/BF00480768

Methods have been developed for the synthesis of 3-cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione and 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines, and their structures have been studied.X-ray diffraction examination has shown that these compounds contain a disordered contact between the free electron pair of the pyridine nitrogen and the ?-bond of the allyl grouping, so that they react stereoselectively with halogens to give thiazolo<3,2-a>-1,5-naphthyridinium salts.