Chemoselective synthesis of multisubstituted pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione through a cascade reaction

IF 2.2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of the Iranian Chemical Society Pub Date : 2024-05-05 DOI:10.1007/s13738-024-03023-9

Abdolali Alizadeh, Reihaneh Moterassed

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Abstract

A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and α-aminomaleimides as readily accessible starting materials. In this chemoselective, metal catalyst-free approach Michael addition/intramolecular cyclization and elimination of acetone and carbon dioxide occur consecutively. The significant advantages of this strategy are creating a C–N and a C–C bond, short reaction times, excellent yields (68–80%), and a metal-free catalyst.

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通过级联反应化学选择性合成多取代吡咯并[3,4-b]吡啶-2,5,7(6H)-三酮

通过 3-甲酰基色酮、梅尔德伦酸和α-氨基马来酰亚胺作为易得起始原料的级联反应，提出了一种直接合成多取代 6-烷基-4-色烯基-1-芳基-3,4-二氢-1H-吡咯并[3,4-b]吡啶-2,5,7(6H)-三酮衍生物的简单而高效的方法。在这种化学选择性、无金属催化剂的方法中，丙酮和二氧化碳的迈克尔加成/分子内环化和消除反应连续进行。这种方法的显著优点是可以形成 C-N 和 C-C 键，反应时间短，产率高（68-80%），而且不使用金属催化剂。图表摘要

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来源期刊

Journal of the Iranian Chemical Society 化学-化学综合

CiteScore

4.40

自引率

8.30%

发文量

230

审稿时长

5.6 months

期刊介绍： JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.