Synthesis of 1,3,4-thiadiazol-2(3 H )-one derivatives via an unexpected intramolecular addition-elimination reaction of 1,3,4-thiadiazoles
      
Yazarlar (4)
Hakan Tahtacı
Karabük Üniversitesi, Türkiye
Mustafa Er
Karabük Üniversitesi, Türkiye
Doç. Dr. Tuncay KARAKURT Kırşehir Ahi Evran Üniversitesi, Türkiye
Kemal Sancak
Karadeniz Technical University, Türkiye
Makale Türü Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı Tetrahedron
Dergi ISSN 0040-4020 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Makale Dili İngilizce Basım Tarihi 07-2017
Cilt / Sayı / Sayfa 73 / 30 / 4418–4425 DOI 10.1016/j.tet.2017.06.006
Makale Linki https://linkinghub.elsevier.com/retrieve/pii/S0040402017306257
Özet
A new synthesis was developed for 1,3,4-thiadiazol-2(3H)-one derivatives, based on a new arrangement on the thiadiazole ring with an intramolecular addition-elimination reaction.
To this end, starting from 5-methyl-1,3,4-thiadiazole-2-thiol (1), derivatives of 3-((un)substituted benzyl)-5-methyl-1,3,4-thiadiazol-2(3H)-one (7a-g) and ((un)substituted phenyl)-2-oxoethyl)-5-methyl,3,4-thiadiazol-2(3H)-one (10-15) were synthesized (in yields of 81-88% and 63-71%, respectively). The structures of all synthesized compounds were characterized using IR, H-1 NMR, and C-13 NMR spectroscopy, and elemental analysis, mass spectroscopy and X-ray diffraction analysis (compounds 3c, 7b-f and 10) techniques.
This study presents a new and effective reaction path for the synthesis of 1,3,4-thiadiazol-2(3H)-one derivatives. (C) 2017 Elsevier Ltd. All rights reserved.
Anahtar Kelimeler
1,3,4-Thiadiazole | 1,3,4-Thiadiazol-2(3H)-one | Intramolecular addition-elimination reaction | A novel method