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Synthesis 2005(8): 1228-1230  
DOI: 10.1055/s-2005-861868
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

An Unusual Synthesis of Tröger’s Bases Using DMSO/HCl as Formaldehyde Equivalent

Zhong Li*a,b, Xiaoyong Xua, Yanqing Penga, Zhaoxing Jianga, Chuanyong Dinga, Xuhong Qian*b
a Shanghai Key Lab of Chemistry Biology, Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology, P.O. Box 544,130, Meilong Road Shanghai 200237, P. R. China
b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, P. R. China
Fax: +86(21)64252603; e-Mail: lizhong@ecust.edu.cn;
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Received 3 December 2004
Publikationsdatum:
10. März 2005 (online)

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Abstract

The reactions between anilines and DMSO/HCl produce Tröger’s bases in moderate yield. The Tröger’s bases bearing an electron-withdrawing group can also be synthesized through this procedure. In this reaction, DMSO/HCl acts as formaldehyde equivalent.

Key words

Tröger’s bases - DMSO/HCl - formaldehyde equivalent