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

Gejjalagere S. Lingaraju, Toreshettahally R. Swaroop, Ajjampura C. Vinayaka, Kothanahally S. Sharath Kumar, Marilinganadoddi P. Sadashiva*, Kanchugarakoppal S. Rangappa*

*Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India, Email: rangappaksuni-mysore.ac.in, mpsadashivagmail.com

G. S. Lingaraju, T. R. Swaroop, A. C. Vinayaka, K. S. S. Kumar, M. P. Sadashiva, K. S. Ragappa, Synthesis, 2012, 44, 1373-1379.

DOI: 10.1055/s-0031-1290762 (free Supporting Information)


Abstract

Base-induced cyclization of active methylene isocyanides such as tosylmethyl isocyanide, ethyl isocyanoacetate, and arylmethyl isocyanides with methyl arene- and hetarenecarbodithioates enables an efficient synthesis of 4,5-disubstituted thiazoles. This synthesis is simple, rapid, and often avoids purification steps.


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Key Words

thiazoles, isocyanides, cyclization, dithioesters, click reaction


ID: J66-Y2012-1200