Journal
ORGANIC LETTERS
Volume 24, Issue 46, Pages 8493-8497Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03349
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Funding
- National Natural Science Foundation of China
- Science & Technology Department of Sichuan Province
- Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine
- Xinglin Scholar Research Promo-tion Project of Chengdu University of TCM
- China Postdoctoral Science Foundation
- [22001024]
- [82073998]
- [2022JDRC0045]
- [2021YJ0402]
- [2022JDRC0125]
- [ZYYCXTD-D-202209]
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In this study, a straightforward and efficient method for the synthesis of tetracyclic hydropyrrolo-[3,2-b]indole scaffolds was developed through a cascade reaction of oxindole-derived nitrones with allenoates. Multiple bond formations and cleavage could be achieved using a simple catalyst under mild conditions.
Hydropyrrolo[2,3-b]indole is a privileged indoline motif, while its analogue, hydropyrrolo[3,2-b]indole, has been much less explored. Herein, we developed a cascade reaction of oxindole-derived nitrones with allenoates, providing straightforward access to the tetracyclic hydropyrrolo-[3,2-b]indole scaffolds. Formation of multiple C-C/C-X bonds and cleavage could be achieved within one synthetic step using a simple catalyst (Gimeracil) under mild conditions. The reaction pathway may involve the generation of spiro-hydroazepinone as the key intermediate.
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