I 2 -Triggered N-O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles

A facile and complementary [3 + 2 + 1] annulation of aryl ketoxime acetates and 3-formylindoles to give pyridine derivatives is reported. The condensation reaction demonstrated that I2 was capable of triggering N-O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-11, Vol.16 (46), p.9030-9037
Main Authors: Gao, Qinghe, Wang, Yakun, Wang, Qianqian, Zhu, Yanping, Liu, Zhaomin, Zhang, Jixia
Format: Article
Language:English
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Summary:A facile and complementary [3 + 2 + 1] annulation of aryl ketoxime acetates and 3-formylindoles to give pyridine derivatives is reported. The condensation reaction demonstrated that I2 was capable of triggering N-O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron transfer pathway. This direct and operationally simple protocol provides a fundamental platform to synthesize 3-(4-pyridyl)indoles with high functional group compatibility and high regioselectivity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02230e