Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 22, Pages 15114-15119Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01593
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Funding
- National Natural Science Foundation of China
- Doctoral Research Initiation Fund of Shaoxing University
- [21677101]
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In this study, a novel compound, triazolo[1,2-a]indoline, was synthesized successfully by the oxidative cyclization between NH-indoles and azomethine imines under metal-free and mild conditions. This finding provides a rapid approach for the tri-functionalization of NH-indoles.
Establishing three-dimensional chemicals by using the C2-C3 Z bond of indoles has always been a research hotspot in organic synthesis; however, employing the oxidative C2-C3 Z bond of indoles to generate imine which would lead to the N1-C2 Z bond cyclization under metal-free conditions is still rare. Here, we report a bio-inspired synthesis of triazolo[1,2-a]indolines by the oxidative cyclization between NH-indoles and azomethine imines with 3,3-dimethyldioxirane as the sole oxidant under metal-free and mild conditions. This finding represents an elegant instance of tri-functionalization of NH-indoles, which provides rapid access to a broad range of triazolo[1,2-a]indolines with tetrahydroisoquinolines in one single step. Up to 86% yield and above 20:1 dr value are observed. The radical mechanism and proton migration process have been speculated.
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