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Synthesis of Tetrasubstituted Thiophenes Starting from Amino Mercaptoacrylates and α-brominated Acetamides

[ Vol. 25 , Issue. 6 ]

Author(s):

José Agustín Quincoces Suárez, Alfredo Peña Ricardo, José Matheus Freitas Costa, Carolina Passarelli Gonçalves, Mário Augusto Tremante and Manuel Salustiano Almeida Saavedra*   Pages 748 - 756 ( 9 )

Abstract:


Some thiophenic derivatives show important biological activity or are used as intermediates in organic synthesis. For this reason, it is very important to develop new synthesis procedures with good yields and using few synthesis steps. The present work offers an overview of the method for obtaining substituted thiophenes reported in the literature, and the synthetic procedures used from push-pull systems. In this work, we present the synthesis of 14 new tetrasubstituted thiophenes starting from amino mercaptoacrylates and α-brominated acetamides, derived from furoyl and benzoylacetonitrile, respectively. Best yields (66 to 85%) were obtained through ultrasonic irradiation. Combined use of spectroscopic methods and elementary analysis was done for characterization of all the compounds.

Keywords:

Thiophenes, α-brominated acetamides, aroylacetonitriles, amino mercaptoacrylates salts, push-pull.

Affiliation:

Department of Pharmacy and Department of Biotechnology and Health Innovation, Anhanguera University of Sao Paulo, Avenida Raimundo Pereira Magalhaes 3305, 05145-200, Pirituba, Sao Paulo, SP, Department of Exacted Science. Chemistry Sections, Higher Institute of Educational Sciences of Huila, Rua Sarmento Rodrigues S/N, CP:230, Lubango, Huila, Center for Natural and Human Sciences, Federal University of ABC, Avenida dos Estados 5001, 09210-580, Bangu, Santo Andre, SP, Department of Pharmacy and Department of Biotechnology and Health Innovation, Anhanguera University of Sao Paulo, Avenida Raimundo Pereira Magalhaes 3305, 05145-200, Pirituba, Sao Paulo, SP, Department of Pharmacy and Department of Biotechnology and Health Innovation, Anhanguera University of Sao Paulo, Avenida Raimundo Pereira Magalhaes 3305, 05145-200, Pirituba, Sao Paulo, SP, Chemical Synthesis Laboratory. Center for Biological and Health Sciences, Mackenzie Presbyterian University, Rua da Consolacao 930, 01302-907, Consolacao, Sao Paulo, SP

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