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Synthesis of heterocyclic compounds using amidines as their ene‐1,1‐diamine tautomers. I. Synthesis of 4,5‐dihydro‐3 H ‐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
Author(s) -
Ito Kunio,
Kizuka Yoshiko,
Hirano Yuji
Publication year - 2005
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.5570420417
Subject(s) - tautomer , chemistry , diamine , dimethyl acetylenedicarboxylate , methyl acrylate , ene reaction , adduct , medicinal chemistry , acrylate , amidine , organic chemistry , cycloaddition , catalysis , polymer , monomer , copolymer
N ‐ t ‐Butylacetamidines 1 on heating with methyl acrylate ( 2 ) at 200° gave the 4,5‐dihydro‐3 H ‐pyridin‐2‐one 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 ethylenetri‐carboxylate ( 9 ) or dimethyl acetylenedicarboxylate ( 12 ) afforded 3,4‐dihydropyrrol‐2‐one 11 or 1,3‐dihy‐dropyrrol‐2‐one derivatives 13 .