Synthesis 2012; 44(9): 1373-1379
DOI: 10.1055/s-0031-1290762
paper
© Georg Thieme Verlag Stuttgart · New York

An Easy Access to 4,5-Disubstituted Thiazoles via Base-Induced Click Reaction of Active Methylene Isocyanides with Methyl Dithiocarboxylates

Gejjalagere S. Lingaraju
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
,
Toreshettahally R. Swaroop
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
,
Ajjampura C. Vinayaka
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
,
Kothanahally S. Sharath Kumar
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
,
Marilinganadoddi P. Sadashiva*
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
,
Kanchugarakoppal S. Rangappa*
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Fax: +91(821)2500846   Email: rangappaks@gmail.com   Email: rangappaks@uni-mysore.ac.in   Email: mpsadashiva@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 17 January 2012

Accepted after revision: 24 February 2012

Publication Date:
05 April 2012 (online)


Abstract

An efficient synthesis of 4,5-disubstituted thiazoles via base-induced cyclization of active methylene isocyanides such as tosylmethyl isocyanide, ethyl isocyanoacetate, and arylmethyl isocyanides with methyl arene- and hetarenecarbodithioates is reported. This synthesis could be a new click chemistry reaction, since it is simple, rapid, and often avoids purification steps. In addition, this method allow us a clear and general synthesis of novel 4,5-diarylthiazoles.

Supporting Information