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Reactions of 2,2,4,4‐tetramethyl‐1,3‐cyclobutanedione with amines and other nucleophiles. II
Author(s) -
Hansen Gary R.,
Demarco Ronald A.
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060304
Subject(s) - chemistry , nucleophile , steric effects , amide , imine , hydrolysis , medicinal chemistry , primary (astronomy) , organic chemistry , catalysis , physics , astronomy
The reaction of 2,2,4,4‐tetramethyl‐1,3‐cyclobutanedione with various nucleophiles has been demonstrated to be dependent on the reaction conditions, steric factors and the nucleophilicity of the attacking species. In the reaction with primary amines the intermediate has been established as the N ‐substituted imine which is hydrolyzed to the corresponding amide in the presence of water. The reaction of diamines with the dione has been shown to be a method of synthesizing 2‐substituted imidazolines and 1 H ‐4,5‐dihydropyrimidines.