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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(4H)-ones

✍ Scribed by Gorazd Soršak; Branko Stanovnik; Simona GoliČ Grdadolnik

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
288 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

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.

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The synthesis of methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate. The synthesis of trisubstituted pyrroles, 3-amino-2H-pyran-2-ones, fused 2H-pyran-2-ones and 4H-pyridin-4-ones
✍ Renata Toplak; Jurij Svete; Branko Stanovnik; Simona GoliČ Grdadolnik 📂 Article 📅 1999 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 636 KB

Methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate (2) was prepared from methyl \(\mathrm{N}\)-(benzyloxycarbonyl)glycinate (1) and \(t\)-butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-(benzyloxycarbonyl)amino-4 \(\mathrm{H}\)-quinolizin-4-ones 5 and