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Nitrogen bridgehead compounds. Part 83 . Synthesis and ring transformation of 6‐methyl‐4‐oxo‐4 H ‐pyrido[1,2‐ a ]pyrimidine‐3‐acrylates
Author(s) -
Hermecz István,
Horváth Agnes
Publication year - 1992
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.5570290246
Subject(s) - chemistry , pyrimidine , ring (chemistry) , substituent , isomerization , methyl acrylate , acrylate , stereochemistry , transformation (genetics) , side chain , medicinal chemistry , organic chemistry , polymer , catalysis , biochemistry , monomer , copolymer , gene
The thermal ring transformation of 2‐substituted 4‐oxo‐4 H ‐pyrido[1,2‐ a ]pyrimidine‐3‐acrylates gave 2‐substituted 1,8‐naphthyridine‐3‐acrylates, pyrano‐1,8‐naphthyridines and anthyridine, depending upon the nature of the 2‐substituent. A longer reaction period and a higher reaction temperature favored the formation of tricyclic products from 1,8‐naphthyridine‐3‐acrylate after isomerization of the side‐chain at position 3. The products were characterized by means of uv, ir and 1 H nmr spectroscopy.