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

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 (...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 5; p. 1163
Main Authors Yuan, Wei-Cheng, Zeng, Hai-Ying, Zhang, Yan-Ping, Zhao, Jian-Qiang, You, Yong, Yin, Jun-Qing, Zhou, Ming-Qiang, Wang, Zhen-Hua
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 05.03.2024
MDPI
Subjects
2-nitrobenzofurans
cycloaddition reactions
dearomatization
heterocycles
Investigations
Natural products
Nitrogen
para-quinamines
para-quinamines
2-nitrobenzofurans
cycloaddition reactions
heterocycles
dearomatization
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Summary: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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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29051163