Synlett 2017; 28(17): 2281-2284
DOI: 10.1055/s-0036-1590811
letter
© Georg Thieme Verlag Stuttgart · New York

Base-Induced Cyclization of Active Methylene Isocyanides with Xanthate Esters: An Efficient Method for the Synthesis of 5-Alkoxy-4-(tosyl/ethoxycarbonyl)-1,3-thiazoles

Narasimhamurthy Rajeeva, Toreshettahally R. Swaroopb, Seegehalli M. Anila, Yadaganahalli K. Bommegowdaa, Kanchugarakoppal S. Rangappa*a, c, Marilinganadoddi P. Sadashiva*a, c
  • aDepartment of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
  • bDepartment of Studies in Organic Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India
  • cInstitution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangothri, Mysuru, Karnataka 570 006, India   Email: mpsadashiva@gmail.com   Email: rangappaks@gmail.com
Further Information

Publication History

Received: 15 April 2017

Accepted after revision: 02 June 2017

Publication Date:
13 July 2017 (eFirst)

Abstract

Sodium hydride-induced cyclization of 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene or ethyl isocyanoacetate with various xanthate esters gave 5-alkoxy-4-tosylthiazoles or ethyl 5-alkoxythiazol-4-ylcarboxylates, respectively, in good to excellent yields. The xanthate ester S-methyl O-phenyl dithiocarbonate gave 5-(methylsulfanyl)-4-tosyl-1,3-thiazole when treated with 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene under similar conditions.

Supporting Information