Synthesis of 1,3-Dihydrobenzo[c]thiophene-imines via Tandem
Reactions of o-(1-Alkynyl)benzamides
and Lawesson’s Reagent

Qiuping Ding; Xianjin Liu; Hongming Wang; Min Chen; Yiyuan Peng

doi:10.1055/s-0031-1289722

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Synthesis 2012(6): 920-926
DOI: 10.1055/s-0031-1289722

PAPER

Synthesis of 1,3-Dihydrobenzo[c]thiophene-imines via Tandem Reactions of o-(1-Alkynyl)benzamides and Lawesson’s Reagent

Qiuping Ding*^a, Xianjin Liu^a, Hongming Wang^b, Min Chen^a, Yiyuan Peng*^a
^a Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry and Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang 330022, P. R. of China
Fax: +86(791)88120396; e-Mail: dqpjxnu@gmail.com; e-Mail: yiyuanpeng@yahoo.com;
^b Institute for Advanced Study, Nanchang University, Nanchang, 330031, P. R. of China

Weitere Informationen

Publikationsverlauf

Received 8 November 2011
Publikationsdatum:
27. Februar 2012 (online)

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Abstract

Metal-free, one-pot tandem reactions of o-(1-alkynyl)benzamides proceed smoothly in the presence of Lawesson’s reagent leading to 1,3-dihydrobenzo[c]thiophene-imine derivatives in moderate to excellent yields under mild conditions. The method is highly regiospecific for the o-(1-alkynyl)benzothioamide, and only the five-membered-ring product is generated via a 5-exo-dig cyclization involving the sulfur atom.

Key words

o-(1-alkynyl)benzothioamides - tandem reaction - Lawesson’s reagent - metal-free - heterocycles

Supporting Information

References

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