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The synthesis of ethyl 2‐[(2,2‐dibenzoyl)ethenyl]amino‐3‐dimethyl‐aminopropenoate and its application to the synthesis of fused 3‐aminopyran‐2‐ones and 3‐aminoazolo‐ and ‐azinopyrimidin‐4(4 H )‐ones
Author(s) -
Soršak Gorazd,
Stanovnik Branko,
Grdadolnik Simona GoliČ
Publication year - 1998
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.5570350606
Subject(s) - chemistry , yield (engineering) , diethylamine , hydrazine (antidepressant) , reagent , hydrate , organic chemistry , medicinal chemistry , chromatography , metallurgy , materials science
Abstract Ethyl 2‐[(2,2‐dibenzoyl)ethenyl]amino‐3‐dimethylaminopropenoate ( 3 ) was prepared from dibenzoylmethane ( 1 ) in two steps, and used as a reagent for preparation of fused substituted 3‐aminopyranones 12–15 in over 90% yield, quinolizin‐4‐one 16 in over 79% yield, and fused pyrimidin‐4‐ones 17–19 in 40–50% yield. Deprotection of (2,2‐dibenzoyl)ethenyl group with either diethylamine or hydrazine hydrate produced free amino compounds 20, 21 and 22 in 35%, 91% and 71% yield, respectively.