Autocatalytic Nucleophilic Substitution of Hydroxylactam by Thiophenol: Access to N(acyl), S-acetals

Author(s): Fei Qi, Rou Li, Fang Fang, Pengfei Li*

Journal Name: Current Green Chemistry

Volume 3 , Issue 3 , 2016

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Graphical Abstract:


Background: Catalyst-free nucleophilic substitution between hydroxylactam and thiol was developed for the construction of N (acyl), S-acetal skeletons.

Methods: The new protocol provides a series of isoindolo-β-carboline-derived N (acyl), S-acetals in high yields.

Result: The methodology has many advantages, such as catalyst-free, mild reaction conditions, simple operations, high atom-economy, and water as by-product and so on. The reaction mechanism was also discussed.

Keywords: Catalyst-free, nucleophilic substitution, alcohol, thiophenol, hydroxylactam, N-acylimium ion, N, S-acetal.

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Article Details

Year: 2016
Published on: 27 April, 2017
Page: [235 - 241]
Pages: 7
DOI: 10.2174/2213346104666170130144609
Price: $25

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