

Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine
Moustafa Ahmed Gouda (1,*)


(1) Chemistry Department, Faculty of Science, Mansoura University, Mansoura 35516, Egypt
(2) Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
(*) Corresponding Author
Received: 18 Jul 2014 | Revised: 01 Aug 2014 | Accepted: 23 Aug 2014 | Published: 31 Dec 2014 | Issue Date: December 2014
Abstract
Condensation of cyanoacetamide 3 with cycloalkanones and elemental sulfur in the presence of morpholine yielded the bisthiophenes 4 and 5. Also, its (3) condensation with terphthalaldehyde or coupling with p-phenylenedidiazonium chloride afforded compound 13 and 14, respectively. Furthermore, cyanoacetylation of compound 4 or 5 afforded the cyanoacetamides 6 and 7, respectively. Knoevenagel condensation of compound 7 with aromatic aldehyde afforded the arylidenes 10, 11 and coumarin 12, respectively. Treatment of compound 3 with CS2 in DMF/KOH followed by alkylation reaction with ethyl bromoacetate afforded the triester derivative 16, which gave 3-aminothiophene 17 upon heating in DMF/TEA. Moreover, refluxing of compound 23 with α-haloketones afforded 3-aminothiophenes 24 and 25. Identity of newly synthesized compounds was established by the spectral data and novel compounds were evaluated as antioxidant agents.
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DOI: 10.5155/eurjchem.5.4.644-651.1125
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Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Citations
[1]. Rangappa S. Keri, Karam Chand, Srinivasa Budagumpi, Sasidhar Balappa Somappa, Siddappa A. Patil, Bhari Mallanna Nagaraja
An overview of benzo [b] thiophene-based medicinal chemistry
European Journal of Medicinal Chemistry 138, 1002, 2017
DOI: 10.1016/j.ejmech.2017.07.038

[2]. Moustafa A. Gouda, Belal H.M. Hussein, Amr El-Demerdash, Mona E. Ibrahim, Mohammed A. Salem, Mohamed H. Helal, Wafaa S. Hamama
A Review: Synthesis and Medicinal Importance of Coumarins and their Analogues (Part II)
Current Bioactive Compounds 16(7), 993, 2020
DOI: 10.2174/1573407215666191111120604

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DOI Link: https://doi.org/10.5155/eurjchem.5.4.644-651.1125

















European Journal of Chemistry 2014, 5(4), 644-651 | doi: https://doi.org/10.5155/eurjchem.5.4.644-651.1125 | Get rights and content
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