Synthesis of some alkylaminothiophene derivatives from 3,4-dibromothiophene and their theoretical calculations

Ermis E., Berber H., GÜLLÜ M.

TETRAHEDRON, cilt.75, sa.33, ss.4577-4590, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 75 Sayı: 33
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.tet.2019.06.049
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.4577-4590
  • Anahtar Kelimeler: 3,4-Dibromothiophene, 3,4-(N,N '-dialkylamino)thiophene, 3-(N-alkylamino) thiophene, Copper catalyzed amination, DMEA, DFT, PALLADIUM-CATALYZED AMINATION, SPECTROSCOPIC CHARACTERIZATION, PHOTOPHYSICAL PROPERTIES, THIOPHENE DERIVATIVES, ELECTRODE MATERIALS, DFT CALCULATIONS, SCHIFF-BASE, HOMO-LUMO, C-13 NMR, FT-IR
  • Anadolu Üniversitesi Adresli: Hayır

Özet

In this study, the copper catalyzed amination reactions of 3,4-dibromothiophene with some primary, cyclic and acyclic secondary amines were investigated to prepare novel electron rich-thiophenes which are expected to be used as novel N-containing donor type monomer candidates for conductive polymers. In order to obtain better yields, this SNAr type amination reaction was optimized by studying the reaction conditions, such as the copper catalyst, the type of copper source, the presence of a base and the type of the solvent on the model reaction between 3,4-dibromothiophene and n-butylamine. A variety of 3,4-(N,N'-dialkylamino)thiophenes and 3-(N-alkylamino)thiophenes were synthesized in moderate yields under the optimized reaction conditions. In addition, two new heterocyclothiophene derivatives were successfully prepared from the cyclization reaction of 3,4-bis(N-butylamino)thiophene. The characterization of the isolated alkylaminothiophenes was performed by FTIR, H-1 and C-13 NMR, GCMS and elemental analysis. The theoretical calculations for all alkylaminothiophenes were executed by using the DET/B3LYP/6-311+G(2d,p) approach. (C) 2019 Elsevier Ltd. All rights reserved.