Please use this identifier to cite or link to this item: https://hdl.handle.net/20.500.13087/808
Title: Synthesis of some alkylaminothiophene derivatives from 3,4-dibromothiophene and their theoretical calculations
Authors: Ermiş, Emel
Berber, Halil
Güllü, Mustafa
Keywords: 3,4-Dibromothiophene
3,4-(N,N '-dialkylamino)thiophene
3-(N-alkylamino) thiophene
Copper catalyzed amination
DMEA
DFT
Issue Date: 2019
Publisher: Pergamon-Elsevier Science Ltd
Abstract: 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.
URI: https://doi.org/10.1016/j.tet.2019.06.049
https://hdl.handle.net/20.500.13087/808
ISSN: 0040-4020
Appears in Collections:Matematik Bölümü Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu
WoS İndeksli Yayınlar Koleksiyonu

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