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Synthesis 2018; 50(03): 575-582
DOI: 10.1055/s-0036-1591505
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Aryl-3-arylthio-3,4-dihydroquinolin-2(1H)-ones via Cyclization of N-Arylcinnamamides with N-Thiosuccinimides

Hexiang Ren
a   College of Chemistry and Chemical Engineering and Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Normal University (Yaohu Campus), 99 Ziyangdadao, Nanchang, Jiangxi 330022, P. R. of China
,
Ming Zhang*
a   College of Chemistry and Chemical Engineering and Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Normal University (Yaohu Campus), 99 Ziyangdadao, Nanchang, Jiangxi 330022, P. R. of China
,
Aiqin Zhang*
b   Department of Environmental and Chemical Engineering, Nanchang Hangkong University, Nanchang, Jiangxi 330063, P. R. of China   Email: zmchem@163.com   Email: zmchem@jxnu.edu.cn
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (Grant No. 21262017 and No. 21366023), Jiangxi Provincial Department of Science and Technology (Grant No. 20132BAB203035), and Jiangxi Provincial Department of Education (Grant No. GJJ13531).
Further Information

Publication History

Received: 04 August 2017

Accepted after revision: 03 October 2017

Publication Date:
19 October 2017 (online)

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Abstract

cis-4-Aryl-3-arylthio-3,4-dihydroquinolin-2(1H)-ones were synthesized via electrophilic sulfenylation and cyclization of N-arylcinnamamides with N-arylthiosuccinimides in the presence of boron tri­fluo­ride etherate. The cis-products were obtained with high stereoselectivity.

Key words

cylization - electrophilic reaction - sulfenylation - N-arylcinnamamides - N-arylthiosuccinimides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591505.
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