New reactions of phosgene with tertiary amines

Article abstract of DOI:10.3987/COM-97-S37

1-Benzylwye (3) underwent substitution at the 7-position in the presence of COCl₂ and pyridine in THF to afford various products depending upon the post-treatment through 1,4-dihydropyridine (7) and carboxylic acid derivative (8). When Et₃N was used instead of pyridine, it reacted with COCl₂ to provide two enamines (18 and 19), together with diethylcarbamyl chloride (20), after treatment of the reaction mixture with MeOH.