Paper
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(4H)‐ones
Published Nov 1, 1998 · Gorazd Soršak, B. Stanovnik, S. Grdadolnik
Journal of Heterocyclic Chemistry
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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.
Ethyl 2-[(2,2-dibenzoyl)ethenyl]amino-3-dimethylaminopropenoate (3) effectively synthesizes fused 3-aminopyranones, quinolizin-4-ones, and fused pyrimidin
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