Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. An attempt to prepare benzoylamino substituted azolo‐ and azinopyrimidines with a bridgehead nitrogen atom

doi:10.1002/JHET.5570270247

Paper

Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. An attempt to prepare benzoylamino substituted azolo‐ and azinopyrimidines with a bridgehead nitrogen atom

Published Feb 1, 1990 · B. Stanovnik, H. V. D. Bovenkamp, J. Svete

Journal of Heterocyclic Chemistry

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Abstract

Methyl 2-benzoylamino-3-dimethylaminopropenoate (2) was introduced as a new reagent for the preparartion of fused pyrimidinones 4 from heterocyclic α-amino compounds in acetic acid. In this manner, derivatives of pyrido[1,2-a]pyrimidine 4a,b,f, pyrimido[1,2-b]pyridazine 4g, pyrimido[1,2-c]pyrimidine 4j, pyrazino[1,2-a]pyrimidine 4k, thiazolo[2,3-b]pyrimidine 4l, pyrazolo[1,5-a]pyrimidine 4m, and 1,2,4-triazolo[1,5-a]pyrimidine 4n were prepared.

Study Snapshot

Methyl 2-benzoylamino-3-dimethylaminopropenoate is a promising reagent for the synthesis of fused pyrimidinones with bridgehead nitrogen atoms in heterocyclic systems.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. An attempt to prepare benzoylamino substituted azolo‐ and azinopyrimidines with a bridgehead nitrogen atom

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References

Methyl 2-benzoylamino-3-dimethylaminopropenoate in the synthesis of heterocyclic systems. The synthesis of benzoyl- amino substituted 7H-pyrano[2,3-d]pyrimidine, 1H,6H-pyrano- [2,3-c]pyrazole and 2H-1-benzopyran derivatives†

Methyl 2-benzoylamino-3-dimethylaminopropenoate is a novel method for the synthesis of condensed pyranones, offering a novel procedure for the preparation of condensed pyranones.

The synthesis of β‐heteroarylamino‐α,β‐dehydro‐α‐amino acid and β‐heteroarylamino‐α‐amino acid derivatives

-heteroarylamino-,-dehydro--amino acid and -heteroarylamino-amino acid derivatives were successfully synthesized from heteroarylaminomethyleneoxazolones.

REACTIONS OF 4-ETHOXYALKYLIDENE-2-PHENYL-2-OXAZOLIN-5-ONES WITH 1,3-BINUCLEOPHILIC HETEROAROMATIC SYSTEMS

One-pot syntheses of pyrido[l,2-blpyrimidine] and thiazolo[2,3-blpyrimidine] derivatives were achieved by reacting 4-ethoxyalkylidene-2-phenyl-2-oxazolin-5-ones

Citations

Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds

Heterocycles incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds show potential as antibacterial, antiviral, anti-tumor, and hepatoprotective agents due to their diverse biological activities.

Enaminone, Enaminoesters, and Related Compounds in the Metal-Free Synthesis of Pyridines and Fused Pyridines

Enaminones, enaminoesters, and related compounds enable metal-free synthesis of pyridines and fused pyridines, pyridyl-substituted amino acids, hydroxy acids, and polyols.

An efficient synthesis of (E) -(2 -arylpyrazino[1,2 -a ]pyrimidine-4-ylidene)acetonitriles and cyanomethyl appended pyrimidines

This study demonstrates an efficient synthesis of (E)-(2-arylpyrazino[1,2-a]pyrimidine-4-ylidene)acetonitriles and cyanomethyl appended pyrimidines using base-catalyzed ring transformation of functionalized 2H

Bridgehead Nitrogen Thiazolopyrimidines

Bridgehead nitrogen thiazolopyrimidines show promising chemistry, reactivity, biological activity, and potential applications in various fields.

Catalytic hydrogenation of 3‐benzyloxycarbonylaminoazino[1,2‐x]‐azin‐4‐ones. A facile access to 3‐amino‐6,7,8,9‐tetrahydro‐4H‐pyrido[1,2‐a]pyridin‐4‐ones and 3‐Amino‐6,7,8,9‐tetrahydro‐4H‐azino[1,2‐x]pyrimidin‐4‐ones

Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2x]azin4ones provides facile access to 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2a]pyridin

The Synthesis of 2-Substituted 3-Dimethylaminopropenoates and Related Compounds and Their Application to the Synthesis of Heterocyclic Systems

2-Substituted 3-Dimethylaminopropenoates and related compounds can be synthesized using N,N-dimethylforamide dimethyl acetal (DMFDMA) and t-butoxybis(dimethylamino)methane, with potential applications in heterocycl

13C and 15N NMR study of 1,2,4-Triazolo[1,5-a]pyrimidines with one tautomerism-introducing substituent

7-OH and 7-SH substituted 1,2,4-triazolo[1,5-a]pyrimidines exist in an equilibrium of N4H and N3H tautomers, with fast NMR time scales supporting this result.

The synthesis and transformations of ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate, a new reagent in the synthesis of heterocyclic compounds

Ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate (5) is a new reagent for the synthesis of heterocyclic compounds, with potential applications in the synthesis of heteroaryl