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 | Zendy

Ito Kunio | Zendy; Kizuka Yoshiko | Zendy; Hirano Yuji | Zendy

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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 .

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