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Synthesis of heterocyclic compounds using amidines as their ene-1,1-diamine tautomers. I. Synthesis of 4,5-dihydro-3H-pyridin-2-one, 3,4-dihydropyrrol-2-one and 1,3-dihydropyrrol-2-one derivatives by the reaction of amidines with α,β-unsaturated esters

✍ Scribed by Kunio Ito; Yoshiko Kizuka; Yuji Hirano

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 82 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420417

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✦ Synopsis

N-t-Butylacetamidines 1 on heating with methyl acrylate (2) at 200˚ gave the 4,5-dihydro-3H-pyridin-2one derivatives 5. Michael addition of the acetamidines 1 as their ene-1,1-diamine tautomers 1' to 2 and the subsequent cyclization of the adducts gave derivatives 5. Amidines 1 on reaction with trimethyl ethylenetricarboxylate (9) or dimethyl acetylenedicarboxylate (12) afforded 3,4-dihydropyrrol-2-one 11 or 1,3-dihydropyrrol-2-one derivatives 13.

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