Synthesis of 1H,7H,12bH-Pyrano[3’,4’: 5,6]pyrano[3,4-c][1]benzopyran-1- one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations

doi:10.1002/HLCA.201100237

Paper

Synthesis of 1H,7H,12bH-Pyrano[3’,4’: 5,6]pyrano[3,4-c][1]benzopyran-1- one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations

Published 2012 · M. J. Khoshkholgh, M. R. Hosseindokht, S. Balalaie

Helvetica Chimica Acta

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10

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Abstract

The CuI-catalyzed intramolecular oxa-DielsAlder reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes as unactivated terminal alkynes with 4-hydroxy-6-methyl-2H-pyran-2-one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1). A theoretical investigation of the reaction in terms of HOMOLUMO interactions in the gas phase is also reported. The reaction could be regarded as an inverse-electron-demand DielsAlder cycloaddition. The theoretical results are in high agreement with the experimental evidences.

Study Snapshot

The CuI-catalyzed intramolecular oxa-DielsAlder reaction with 2-(prop-2-yn-1-yloxy)benzaldehydes and 4-hydroxy-6-methyl-2H-pyran-2-one yields pyranones with remarkable che

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 1H,7H,12bH-Pyrano[3’,4’: 5,6]pyrano[3,4-c][1]benzopyran-1- one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations

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References

Dihydro-3H-chromeno-[3,4-b][4,7]phenanthrolin-3-oneand Chromeno[4,3-b]pyrano[3,2-f]quinolin-3(13H)-oneDerivatives by Aza-Diels-Alder Reaction

This study demonstrates a single-step process for synthesizing potentially bioactive polycyclic heterocycles in high yields using O-propargylated salicylaldehyde with 6-aminoquinolone and 6-aminocoumarin.

A new domino Knoevenagel-hetero-Diels–Alder reaction: an efficient catalyst-free synthesis of novel thiochromone-annulated thiopyranocoumarin derivatives in aqueous medium

The domino Knoevenagel-hetero-Diels-Alder reaction efficiently synthesizes novel pentacyclic thiochromone-annulated thiopyranocoumarin derivatives in aqueous medium with high regio- and stereo-selectivity

Copper(I)-Catalyst-Free Approachfor the Synthesis of Chromene-Fused Pyrido[3,2-d]pyrimidines by Lewis AcidCatalyzed Aza-Diels-Alder Reaction

This study presents a copper(I)-catalyst-free approach for the synthesized chromene-fused pyrimidines with high yields (71-82%) from easily available starting materials.

Synthesis of Novel Polycyclic Indole‐Annulated Thiopyranocoumarin Derivatives via Domino Knoevenagel–Hetero‐Diels–Alder Reaction in Aqueous Media

The Domino Knoevenagel-hetero-Diels-Alder reaction efficiently synthesizes novel polycyclic indole derivatives with high regio- and stereoselectivity in aqueous media.

Catalyst-Free Regioselective Synthesis of Benzopyran-Annulated Thiopyrano[2,3-b]thiochromen-5-(4H)-one Derivatives by Domino-Knoevenagel-hetero-Diels—Alder Reaction of Terminal Alkynes with 4-Hydroxy Dithiocoumarin in Aqueous Medium.

The domino-Knoevenagel-hetero-Diels-Alder reaction enables the regioselective synthesis of novel pentacyclic benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(

Catalyst-free domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes in water: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives

The domino-Knoevenagel-hetero-Diels-Alder reaction efficiently synthesizes indole-annulated thiopyranobenzopyran derivatives in 72-80% yields, with no need for catalysts or Lewis acid.

An efficient ZnO-catalyzed synthesis of novel indole-annulated thiopyrano-chromene derivatives via Domino Knoevenagel-hetero-Diels–Alder reaction

ZnO-catalyzed Domino Knoevenagel-hetero-Diels-Alder reaction efficiently synthesizes novel indole-annulated thiopyrano-chromene derivatives with good to excellent yields.

Citations

Synthesis of chromene-fused heterocycles by the Intramolecular–Diels–Alder Reaction: An overview

The intramolecular-Diels-Alder reaction effectively synthesizes various chromene-fused heterocycles using O-propargyl salicylaldehydes as starting material.

Copper nanoparticles as inexpensive and efficient catalyst: A valuable contribution in organic synthesis

Copper nanoparticles are an inexpensive and efficient catalyst for various organic transformations, offering low catalyst loading, high atom economy, better yields, shorter reaction times, and recyclability.

CuI nanoparticles mediated expeditious synthesis of 2-substituted benzimidazoles using molecular oxygen as the oxidant

CuI nanoparticles provide a quick and efficient method for synthesis of 2-substituted benzimidazoles using molecular oxygen, offering short reaction times, easy isolation, and reusability up to six cycles.

Copper-Catalyzed Aza-Diels-Alder Reaction and Halogenation: An Approach To Synthesize 7-Halogenated Chromenoquinolines.

Copper-catalyzed aza-Diels-Alder reaction and halogenation effectively synthesize 7-halogenated chromenoquinolines in satisfactory yields under mild conditions.

Trifluoroethanol as an efficient reaction media for the synthesis of pyran skeleton through domino Knoevenagel–hetero-Diels–Alder reaction with non-activated alkynes

Trifluoroethanol is an efficient media for the synthesis of pyran skeletons with non-activated alkynes, offering short reaction times, easy work-up, good to high yields, and mild reaction conditions.