Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reactio...

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Main Authors: Djenisa H. A. Rocha, Vasco F. Batista, Emanuel J. F. Balsa, Diana C. G. A. Pinto, Artur M. S. Silva
Format: Article
Language:English
Published: MDPI AG 2020-08-01
Series:Molecules
Subjects:
chromene-3-carbaldehydes
3-styryl-2<i>H</i>-chromenes
quinoline-3-carbaldehydes
3<i>H</i>-chromeno[3,4-c]quinolines
3-styrylquinoline-1(2<i>H</i>)-carbaldehydes
Wittig reaction
Online Access:https://www.mdpi.com/1420-3049/25/17/3791
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spelling doaj-069d7f116bfc4545a791b0771ac72c2b2020-11-25T03:42:25ZengMDPI AGMolecules1420-30492020-08-01253791379110.3390/molecules25173791Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic ScaffoldsDjenisa H. A. Rocha0Vasco F. Batista1Emanuel J. F. Balsa2Diana C. G. A. Pinto3Artur M. S. Silva4LAQV-REQUIMTE & Department of Chemistry, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE & Department of Chemistry, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE & Department of Chemistry, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE & Department of Chemistry, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE & Department of Chemistry, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, PortugalChromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reaction of flavanones and azaflavanones. Protocols towards the synthesis of new heterocycles, such as 3<i>H</i>-chromeno[3–<i>c</i>]quinolines, (<i>Z</i>/<i>E</i>)-2-aryl-4-chloro-3-styryl-2<i>H</i>-chromenes, and (<i>E</i>)-2-aryl-4-chloro-3-styrylquinoline-1(2<i>H</i>)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- and quinoline-3-carbaldehydes as building blocks.https://www.mdpi.com/1420-3049/25/17/3791chromene-3-carbaldehydes3-styryl-2<i>H</i>-chromenesquinoline-3-carbaldehydes3<i>H</i>-chromeno[3,4-c]quinolines3-styrylquinoline-1(2<i>H</i>)-carbaldehydesWittig reaction
collection DOAJ
language English
format Article
sources DOAJ
author Djenisa H. A. Rocha
Vasco F. Batista
Emanuel J. F. Balsa
Diana C. G. A. Pinto
Artur M. S. Silva
spellingShingle Djenisa H. A. Rocha
Vasco F. Batista
Emanuel J. F. Balsa
Diana C. G. A. Pinto
Artur M. S. Silva
Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
Molecules
chromene-3-carbaldehydes
3-styryl-2<i>H</i>-chromenes
quinoline-3-carbaldehydes
3<i>H</i>-chromeno[3,4-c]quinolines
3-styrylquinoline-1(2<i>H</i>)-carbaldehydes
Wittig reaction
author_facet Djenisa H. A. Rocha
Vasco F. Batista
Emanuel J. F. Balsa
Diana C. G. A. Pinto
Artur M. S. Silva
author_sort Djenisa H. A. Rocha
title Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
title_short Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
title_full Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
title_fullStr Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
title_full_unstemmed Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
title_sort chromene- and quinoline-3-carbaldehydes: useful intermediates in the synthesis of heterocyclic scaffolds
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-08-01
description Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reaction of flavanones and azaflavanones. Protocols towards the synthesis of new heterocycles, such as 3<i>H</i>-chromeno[3–<i>c</i>]quinolines, (<i>Z</i>/<i>E</i>)-2-aryl-4-chloro-3-styryl-2<i>H</i>-chromenes, and (<i>E</i>)-2-aryl-4-chloro-3-styrylquinoline-1(2<i>H</i>)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- and quinoline-3-carbaldehydes as building blocks.
topic chromene-3-carbaldehydes
3-styryl-2<i>H</i>-chromenes
quinoline-3-carbaldehydes
3<i>H</i>-chromeno[3,4-c]quinolines
3-styrylquinoline-1(2<i>H</i>)-carbaldehydes
Wittig reaction
url https://www.mdpi.com/1420-3049/25/17/3791
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AT emanueljfbalsa chromeneandquinoline3carbaldehydesusefulintermediatesinthesynthesisofheterocyclicscaffolds
AT dianacgapinto chromeneandquinoline3carbaldehydesusefulintermediatesinthesynthesisofheterocyclicscaffolds
AT arturmssilva chromeneandquinoline3carbaldehydesusefulintermediatesinthesynthesisofheterocyclicscaffolds
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