An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine-4-one-5-acetic Acids


YILDIRIM A., ÖZTÜRK S.

CHEMISTRYSELECT, vol.7, no.26, 2022 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 26
  • Publication Date: 2022
  • Doi Number: 10.1002/slct.202201957
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier
  • Keywords: Cyclization, N, N-Disubstituted thiourea, Green chemistry, Lewis acid catalyst, Higher thiazolidines, MICHAEL ADDITION, AMINES, DERIVATIVES, THIAZOLIDIN-4-ONES, POLYMERIZATION

Abstract

For the first time, readily available Ni(II) laurate catalyzed thia-Michael addition of symmetrical N,N-disubstituted thioureas to maleic anhydride and subsequent cyclization in toluene afforded novel thiazolidine-4-one-5-acetic acids with good yields in a short reaction time. The efficiency and low cost of the renewable, eco-friendly laurate based homogenous Lewis acid catalyst and the fact that cyclization proceeds in a much shorter time means that this synthetic method is interesting from a green chemistry point of view. The catalyst can be reused for many times without any significant loss of activity.