Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles

Kuppalli R. Kiran, Toreshettahally R. Swaroop*, Narasimhamurthy Rajeev, Seegehalli M. Anil, Kanchugarakoppal S. Rangappa*, Maralinganadoddi P. Sadashiva*

*University of Mysore, Manasagangothri, Mysuru - 570 006, India, Email: swarooptrgmail.com, rangappaksgmail.com, mpsadashivagmail.com

K. R. Kiran, T. R. Swaroop, N. Rajeev, S. M. Anil, J. S. Rangappa, M. P. Sadashiva, Synthesis, 2020, 52, 1103-1112.

DOI: 10.1055/s-0039-1690821

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Abstract

A cyclization of tosylmethyl isocyanide with α-oxodithioesters in the presence of KOH provides 4-methylthio-5-acylthiazoles, whereas ethyl isocyanoacetate underwent cyclization with α-oxodithioesters to form 4-ethoxycarbonyl-5-acylthiazoles in the presence of DBU/EtOH.

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Key Words

thiazoles, TosMIC, ethyl isocyanoacetate, α-oxodithioester, cyclization

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ID: J66-Y2020