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

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

Volume: 3 Issue: 3

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

Affiliation:

• Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055,China

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

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.

Cite this article as:

Qi Fei, Li Rou, Fang Fang and Li Pengfei*, Autocatalytic Nucleophilic Substitution of Hydroxylactam by Thiophenol: Access to N(acyl), S-acetals, Current Green Chemistry 2016; 3 (3) . https://dx.doi.org/10.2174/2213346104666170130144609

DOI https://dx.doi.org/10.2174/2213346104666170130144609	Print ISSN 2213-3461
Publisher Name Bentham Science Publisher	Online ISSN 2213-347X