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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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 |
work_keys_str_mv |
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_version_ |
1724525194319495168 |