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. 2020 Aug 4;10(48):28720-28724.
doi: 10.1039/d0ra05687a. eCollection 2020 Aug 3.

Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides

Kai-Kai Wang  1 , Yan-Xin Xie  2 , Yan-Li Li  3 , Rongxiang Chen  1 , Zhan-Yong Wang  1
Affiliations

Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides

Kai-Kai Wang et al. RSC Adv. .

Abstract

A highly diastereoselective dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides has been developed. The transformation provides a series of functionalized fused tricyclic benzo[4,5]thieno[2,3-c]pyrroles in good yields (up to 92%) under mild reaction conditions. In addition, a gram-scale experiment and the synthetic transformation of the cycloadduct further highlighted the synthetic utility. The relative configurations of the typical products were clearly confirmed by X-ray crystallography.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Dearomative cycloaddition reaction of electron-deficient heteroarenes with nonstabilized azomethine ylides.
Scheme 2
Scheme 2. Dearomative cycloaddition reaction of 2-nitrobenzothiophene and 2-nitrobenzofuran with nonstabilized azomethine ylide.
Scheme 3
Scheme 3. Scaled-up version of synthesis of fused tricyclic benzo[4,5]thieno[2,3-c]pyrrole.
Scheme 4
Scheme 4. Transformations of product 3a.
See this image and copyright information in PMC

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