CONDENSED PYRIDINES. 6. SYNTHESIS AND STRUCTURE OF ADAMANTYL-, CYCLOPROPYL- AND ALKYL-SUBSTITUTED 3-HALOMETHYL-2,3-DIHYDRO-8-CYANOTHIAZOLOPYRIDINIUM SALTS AND THEIR OXAZOLO AND SELENAZOLO DERIVATIVES

Article abstract of DOI:10.1007/BF00476391

The reaction of substituted 2-cyanopyridin-2(1H)-ones and their thione and selenone derivatives with allyl bromide gives the corresponding 2-allyloxy-, 2-allylmercapto-, and 2-allylseleno-3-pyridines, which upon treatment with halogens, form intramolecular quaternization products, namely, 3-halomethyl-2,3-dihydro-8-cyanooxazole<3,2-a>pyridinium salts and their thiazolo and selenazolo analogs.X-ray diffraction structural analysis was used to determine the structure of 3-bromomethyl-2,3-dihydro-5,7-dimethyl-8-cyanothiazolo<3,2-a>pyridinium perchlorate.