Three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with acetonitriles and 4-hydroxycoumarin. Crystal and molecular structure of ethyl 2-amino-3-cyano-1′-cyclohexyl-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro-[pyrano[3,2-c]chromene-4,3′-pyrrole]-4′-carboxylate

doi:10.1134/S1070428015010121

Paper

Three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with acetonitriles and 4-hydroxycoumarin. Crystal and molecular structure of ethyl 2-amino-3-cyano-1′-cyclohexyl-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro-[pyrano[3,2-c]chromene-4,3′-pyrrole]-4′-carboxylate

Published Feb 15, 2015 · M. V. Dmitriev, P. Silaichev, A. N. Maslivets

Russian Journal of Organic Chemistry

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Abstract

Ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates reacted with malononitrile (methyl cyanoacetate) and 4-hydroxycoumarin to produce substituted ethyl 2-amino-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro[pyrano[3,2-c]chromene-4,3′-pyrrole]-4′-carboxylates. The crystal and molecular structure of ethyl 2-amino-3-cyano-1′-cyclohexyl-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro[pyrano[3,2-c]chromene-4,3′-pyrrole]-4′-carboxylate was determined by X-ray analysis.

Study Snapshot

This study demonstrates the successful three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with acetonitriles and 4-hydroxycoumarin, leading to the crystal and molecular structure of ethyl 2-amino-3-cyano-1

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with acetonitriles and 4-hydroxycoumarin. Crystal and molecular structure of ethyl 2-amino-3-cyano-1′-cyclohexyl-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro-[pyrano[3,2-c]chromene-4,3′-pyrrole]-4′-carboxylate

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References

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Citations

Substrate-dependent regiodivergent three-component condensation of 1H-pyrrole-2,3-diones, malononitrile and 4-hydroxyquinolin-2(1H)-ones

The developed regiodivergent three-component condensation can produce spiro[pyrano[3,2-c]quinoline-4,3′-pyrrole] derivatives or substituted 1,5-dihydropyrrole-2-ones depending on substrate and reaction conditions.

Three-Component Reaction of Pyrrolediones, Malononitrile, and Acyclic Enols

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Synthesis of Spiro Compounds Based on 1H-Pyrrole-2,3-Diones

This review highlights progress in the synthesis of new polyheterocyclic compounds with concomitant formation of quaternary spiro centers, highlighting the importance of stereoselective construction in natural product synthesis.

Reaction of 2-(2-Oxo-1,2-dihydro-3H-pyrrol-3-ylidene)- malononitriles with C-Nucleophiles. Synthesis of New Spiro-Fused Pyrrole Derivatives

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One-pot, three-component synthesis of spiro[indeno[1,2-b]quinoline-10,3'-pyrroles] via the Hantzsch-type reaction of 1H-pyrrole-2,3-diones

This new one-pot, three-component method for synthesis of spiro[indeno[1,2-b]quinoline-10,3'-pyrroles] offers simple, metal-free conditions, easy product isolation, and good yields.

New method for in situ generation of enolate-iminium 1,4-dipoles for [4 + 2] and [4 + 1] dipolar heterocycloaddition reactions

This study demonstrates that dihydropyrazolones react as 1,4-dipoles in most cycloaddition reactions, highlighting their importance in heterocycloaddition reactions.