Synlett
DOI: 10.1055/s-0036-1590862
letter
© Georg Thieme Verlag Stuttgart · New York

A Synthesis of Functionalized Thiazoles and Pyrimidine-4(3H)-thiones from 1,1,3,3-Tetramethylguanidine, Acetylenic Esters, and Aryl Isothiocyanates

Issa Yavari*a, Asiyeh Amirahmadia, Mohammad Reza Halvagarb
  • aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Email: yavarisa@modares.ac.ir
  • bDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
Further Information

Publication History

Received: 06 May 2017

Accepted after revision: 11 July 2017

Publication Date:
25 August 2017 (eFirst)

Abstract

Aryl isothiocyanates react with dialkyl 2-{[bis(dimethylamino)methylene]amino}maleates, generated from 1,1,3,3-tetramethylguanidine and acetylenic esters, to afford 2-(dimethylamino)-1,3-thiazole derivatives, functionalized 2-(dimethylamino)-6-thioxo-1,6-dihydropyrimidines, and ethyl 2-(dimethylamino)-6-[(4-nitrophenyl)im­ino]-4-phenyl-6H-1,3-thiazine-5-carboxylate, in moderate to good yields.

Supporting Information