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Methyl 2‐[bis(acetyl)ethenyl]aminopropenoate in the synthesis of heterocyclic systems
Author(s) -
Selič Lovro,
Stanovnik Branko
Publication year - 1997
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.5570340317
Subject(s) - chemistry , acetylacetone , nucleophile , medicinal chemistry , bicyclic molecule , organic chemistry , catalysis
Methyl 2‐[bis(acetyl)ethenyl]aminopropenoate ( 4 ) was prepared in 3 steps from acetylacetone ( 1 ) via 4‐( N,N ‐dimethylamino)‐3‐acetylbut‐3‐en‐2‐one ( 2 ) and methyl N ‐[2,2‐bis(acetyl)ethenyl]glycinate ( 3 ). Compound 4 reacts with N ‐ and C ‐nucleophiles to give fused heterocyclic systems. Derivatives of pyrido[1,2‐ a ]pyrimidones 14–16 and thiazolo[3,2‐ a ]pyrimidones 17 and 18 were prepared from 2‐aminopyridines and 2‐aminothiazoles, respectively. With C ‐nucleophiles derivatives of pyrido[1,2‐ a ]‐pyridinone 19 and 2 H ‐1‐benzopyran‐2‐one 20–22 were prepared.