Different types of reactions have been found with isomeric tricyclic fused thiazolium salts for their interactions with secondary amines. Thus, the angularly fused quinolinium salt 7 gave rise to a stable pseudobase 8; the related angular isoquinolinium system 9 led to opening of the thiazole ring and enamine 10 was formed; and the linear system 6 underwent opening of the pyridine moiety and gave the aldehyde compound 16. The reactions were interpreted on FMO theory; the CNDO/2 calculation supported the qualitative picture based on the “annelation effect”.
ASJC Scopus subject areas
- Organic Chemistry