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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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,*) , Serry Atta Atta El Bialy (2)

(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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Keywords


Thiocarbamoyl; Cyanoacetylation; 2-Aminothiophene; Antioxidant evaluation; 3,5-Dimethyl-1H-pyrazole; 3-(Ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine

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DOI: 10.5155/eurjchem.5.4.644-651.1125

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Funding information


Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia

Citations

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[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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How to cite


Gouda, M.; El Bialy, S. Eur. J. Chem. 2014, 5(4), 644-651. doi:10.5155/eurjchem.5.4.644-651.1125
Gouda, M.; El Bialy, S. Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine. Eur. J. Chem. 2014, 5(4), 644-651. doi:10.5155/eurjchem.5.4.644-651.1125
Gouda, M., & El Bialy, S. (2014). Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine. European Journal of Chemistry, 5(4), 644-651. doi:10.5155/eurjchem.5.4.644-651.1125
Gouda, Moustafa, & Serry Atta Atta El Bialy. "Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine." European Journal of Chemistry [Online], 5.4 (2014): 644-651. Web. 3 Jun. 2023
Gouda, Moustafa, AND El Bialy, Serry. "Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

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