Visible Light-Induced 6π-Heterocyclization/Dehydroaromatization for Synthesis of Indoloquinolinone Skeletons.

J Org Chem

Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. China.

Published: October 2024

In this work, we report a protocol for the synthesis of an indoloquinolinone skeleton using visible light-induced energy transfer. This method avoids the premodification of substrates and exhibits high yields. For gram-scale reactions, only 0.01 mol % (100 ppm) of photosensitizer is required for rapid conversion. Mechanistic studies revealed that this reaction differs from conventional 6π photocyclization reactions; undergoing a process involving 6π cyclization due to energy transfer and dehydrogenation due to product self-catalysis has been experienced.

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http://dx.doi.org/10.1021/acs.joc.4c01653DOI Listing

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