Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines

Gurdere M. B., Emec A. C., Aslan O. N., Budak Y., Ceylan M.

SYNTHETIC COMMUNICATIONS, cilt.46, sa.6, ss.536-545, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 6
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1080/00397911.2016.1152585
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.536-545
  • Anahtar Kelimeler: 2-Aminoethanethiol hydrochloride, chalcones, 1, 4-thiazephines, triethylamin, CONVERTING ENZYME-INHIBITORS, SOLVENT, DERIVATIVES, DISCOVERY
  • Atatürk Üniversitesi Adresli: Hayır

Özet

The triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcone analogs was investigated. This addition, bearing a 2-thienyl group at the 3-position, gave the only addition adduct at room temperature in 3h, whereas the chalcones bearing the 2-furyl group at the 1-position gave an addition-cyclization product (1, 4-thiazepine) in the same conditions. The effect of the groups to the reaction was investigated by changing the 1- and 3-position groups. The chalcones bearing the 2-thienyl group at the 1-position and the others afforded the mixture of products in different ratio at rt for 0.5-24h. Moreover, the addition-cyclization products (1,4-thiazepine) were obtained under reflux conditions in 36h. The structures of the synthesized compounds were elucidated by H-1 NMR, C-13 NMR, infrared, and elemental analysis.