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

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

Olivier Hebert
a   Université de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
,
Carole Dubouilh-Benard
a   Université de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
,
b   Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2, France
,
b   Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2, France
,
a   Université de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
,
a   Université de Rouen-Normandie (UNIROUEN), INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
› Author Affiliations
This work was partially supported by University of Rouen Normandy, INSA Rouen Normandy, the Centre National de la Recherche Scientifique (CNRS), European Regional Development Fund (ERDF), Labex SynOrg (ANR-11-LABX-0029), Carnot Institute I2C, the graduate school for research Xl-Chem (ANR-18-EURE-0020 XL CHEM), and by Region Normandie.


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.

Supporting Information



Publication History

Received: 20 June 2022

Accepted after revision: 04 July 2022

Accepted Manuscript online:
04 July 2022

Article published online:
22 August 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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