Synthesis of Benzofuro[3,2-]indol-3-one Derivatives Via Dearomative (3 + 2) Cycloaddition of 2-Nitrobenzofurans and -Quinamines

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2024 Mar 13

PMID 38474676

Authors

Wei-Cheng Yuan

Hai-Ying Zeng

Yan-Ping Zhang

Jian-Qiang Zhao

Yong You

Jun-Qing Yin

Ming-Qiang Zhou

Zhen-Hua Wang

Affiliations

Soon will be listed here.

Abstract

An efficient dearomative (3 + 2) cycloaddition of -quinamines and 2-nitrobenzofurans has been developed. This reaction proceeds smoothly under mild conditions and affords a series of benzofuro[3,2-]indol-3-one derivatives in good to excellent yields (up to 98%) with perfect diastereoselectivities (all cases > 20:1 ). The scale-up synthesis and versatile derivatizations demonstrate the potential synthetic application of the protocol. A plausible reaction mechanism is also proposed to account for the observed reaction process. This work represents the first instance of the -triggered dearomative (3 + 2) cycloaddition of 2-nitrobenzofurans.

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