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

doi:10.1002/JHET.5570360135

Paper

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

Published 1999 · R. Toplak, J. Svete, B. Stanovnik

Journal of Heterocyclic Chemistry

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29

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Abstract

Methyl 2-(benzyloxycarbonyl)aimno-3-dimemylaminopropenoate (2) was prepared from methyl N-(benzyloxycarbonyl)glycinate (1) and t-butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-(benzyloxycarbonyl)amino-4H-quinolizin-4-ones 5 and 6, −2H-pyran-2-ones 17–19, −2H-1-benzopyran-2-ones 28–31, and -naphthopyrans 32–35, −2H-pyrano[3,2-c]pyridine-2,5-dione 46, -pyrano-[4,3-b]pyran-2,5-dione 47, -pyrano[3,2-c]benzopyran-2,5-dione 48, -pyrano[2,3-c]pyrazol-6-ones 49 and 50, -pyrano[2,3-d]pyrirnidin-7-ones 51 and 52 derivatives. In the reaction of 2 with 1,3-diketones trisubsti tuted pyrroles 14–16 were formed. Selective removal of benzyloxycarbonyl group was achieved by cat alytic transfer hydrogenation with Pd/C in the presence of cyclohexene to afford free 3-amino compounds 7, 8, 20, 36–38 and 53–57 in yields better than 80%.

Study Snapshot

Methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate can be used to synthesize trisubstituted pyrroles, 3-amino-2H-pyran-2-ones, fused 2H-pyran-2

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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

Ethyl 2-[(2,2-dibenzoyl)ethenyl]amino-3-dimethylaminopropenoate (3) effectively synthesizes fused 3-aminopyranones, quinolizin-4-ones, and fused pyrimidin

Synthesis and transformations of methyl (E)‐2‐(acetylamino)‐3‐cyanoprop‐2‐enoate und methyl (E)‐2‐(benzoylamino)‐3‐cyanoprop‐2‐enoate, versatile reagents for the preparation of polyfunctional heterocyclic systems

Methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate (2a) and its 2-benzoyl analog (2b) are versatile reagents for the preparation of polyfunctional heterocyclic systems, such as pyrroles, pyrimidine

Methyl and Phenylmethyl 2-Acetyl-3-{[2-(dimethylamino)-1-(methoxycarbonyl)ethenyl]amino}prop-2-enoate in the Synthesis of heterocyclic systems: Preparation of 3-amino-4H-pyrido-[1,2-a]pyrimidin-4-ones

Methyl and Phenylmethyl 2-acetyl-3-[2-(dimethylamino)-1-(methoxycarbonyl)ethenyl]amino-prop-2-enoate (4) and (5) were used as reagents for the preparation of

The synthesis and transformation of ethyl 2‐(2‐acetyl‐2‐benzoyl‐1‐ethenyl)amino‐3‐dimethylaminopropenoate. A new synthesis of 2,3,4‐trisubstituted pyrroles

This study presents a new synthesis of 2,3,4-trisubstituted pyrroles using ethyl 2-(2-acetyl-2-benzoyl-1-ethenyl)amino-3-dimethylarninopropenoate, a novel

Alkyl (E,Z)-2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates in the synthesis of fused pyrimidinones. A facile route to 3-aminoazino-4H-pyrimidin-4-ones

This study presents a facile route to 3-aminoazino-4H-pyrimidin-4-ones by using alkyl 2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates and

Citations

Ring switching tricomponent synthesis of pyrano[2,3-b]pyridine multifunctional derivatives

This study successfully synthesized new 3-acylamino-7-hydroxy-5-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6-carbonitriles using the Erlenmeyer-Plöchl reaction conditions, with the solid phase exhibiting hydroxypyridine t

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.

Synthesis of Enediamino Amino Acid Analogues and Peptides

This review reviews methods for synthesizing enediamino amino acid analogues and peptides, highlighting the need for further research on their unique functionality.

A mild and efficient method for large scale synthesis of 3-aminocoumarins and its further application for the preparation of 4-bromo-3-aminocoumarins

Large-scale synthesis of 3-aminocoumarins can be achieved using 70% sulfuric acid under reflux conditions, leading to the preparation of 4-bromo-3-aminocoumarins.

New anticancer agents mimicking protein recognition motifs.

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