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, cilt.7, sa.26, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 7 Sayı: 26
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1002/slct.202201957
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Anahtar Kelimeler: Cyclization, N, N-Disubstituted thiourea, Green chemistry, Lewis acid catalyst, Higher thiazolidines, MICHAEL ADDITION, AMINES, DERIVATIVES, THIAZOLIDIN-4-ONES, POLYMERIZATION
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

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.