Monitoring of Catalyst-Free Microwave-Assisted MCR-Type Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives Using Raman Spectrometry

Olivier Hebert; Carole Dubouilh-Benard; Joana F. Campos; Sabine Berteina-Raboin; Corinne Fruit; Thierry Besson

doi:10.1055/a-1891-0976

Synthesis, Table of Contents

Synthesis 2022; 54(23): 5215-5225
DOI: 10.1055/a-1891-0976

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Monitoring of Catalyst-Free Microwave-Assisted MCR-Type Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives Using Raman Spectrometry

Olivier Hebert

^aUniversité de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France

,

Carole Dubouilh-Benard

^aUniversité de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France

,

Joana F. Campos

^bInstitut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2, France

,

Sabine Berteina-Raboin

^bInstitut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2, France

,

Corinne Fruit

^aUniversité de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France

,

Thierry Besson ∗

^aUniversité de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France

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Abstract

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Abstract

In order to prepare an array of β-cyanoenamine derivatives as potential precursors of heterocyclic systems with pharmaceutical interest, the synthesis of fifteen polyfunctionalized 4H-chromenes was realized via a microwave-assisted and catalyst-free three-component reaction. Microwave-heated reactions were monitored by Raman spectroscopy, enabling a fast and efficient setting of the process parameters. This study confirms that this monitoring tool may have some limitations linked to homogeneity of reaction medium. This work also investigates the use of some bio-sourced and sustainable solvents currently studied in many works. Ethanol remains the most suitable for this synthesis.

Key words

microwave - Raman spectroscopy - real-time monitoring - multicomponent reaction - catalyst free - 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

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References

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