2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one

The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one (<b>1</b>) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a c...

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Bibliographic Details
Main Authors: Ivette Morales-Salazar, Mónica A. Rincón-Guevara, Eduardo González-Zamora, Alejandro Islas-Jácome
Format: Article
Language:English
Published: MDPI AG 2022-11-01
Series:Molbank
Subjects:
Online Access:https://www.mdpi.com/1422-8599/2022/4/M1503
Description
Summary:The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one (<b>1</b>) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade <i>aza</i>-Diels-Alder cycloaddition/<i>N</i>-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product <b>1</b> was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR).
ISSN:1422-8599