3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives

Sayed Abd El-moneim Ahmed Altaweel; Ahmed Abdelhameed Khames; Abu-Bakr Abdelhady Mohamed El-Adasy; Abdallah Mahmoud Ahmed Hassane; Abdel-Haleem Mostafa Hussein

doi:doi:10.11648/j.ajhc.20210702.12

3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives

Sayed Abd El-moneim Ahmed Altaweel, Ahmed Abdelhameed Khames, Abu-Bakr Abdelhady Mohamed El-Adasy, Abdallah Mahmoud Ahmed Hassane, Abdel-Haleem Mostafa Hussein

Published in American Journal of Heterocyclic Chemistry (Volume 7, Issue 2)

Received: 18 March 2021 Accepted: 9 July 2021 Published: 15 July 2021

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Abstract

In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.

Published in	American Journal of Heterocyclic Chemistry (Volume 7, Issue 2)
DOI	10.11648/j.ajhc.20210702.12
Page(s)	26-32
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

3-oxo-butanamide, Thiophene, Thiazole, Thieno[2, 3-d]pyrimidine

References

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[9]	A. M. Hussein, I. M. M. Othman, M. A. M. Gad-Elkareem, A-B. A. El-Adasy and A. A. Khames, "3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Reactions and Biological Evaluation of Novel Thiophene, Pyridine, Pyrimidine, 1,2,4-Triazine Derivatives", Elixir Org. Chem., 106, 46634-46643, (2017).
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Sayed Abd El-moneim Ahmed Altaweel, Ahmed Abdelhameed Khames, Abu-Bakr Abdelhady Mohamed El-Adasy, Abdallah Mahmoud Ahmed Hassane, Abdel-Haleem Mostafa Hussein. (2021). 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. American Journal of Heterocyclic Chemistry, 7(2), 26-32. https://doi.org/10.11648/j.ajhc.20210702.12

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ACS Style

Sayed Abd El-moneim Ahmed Altaweel; Ahmed Abdelhameed Khames; Abu-Bakr Abdelhady Mohamed El-Adasy; Abdallah Mahmoud Ahmed Hassane; Abdel-Haleem Mostafa Hussein. 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. Am. J. Heterocycl. Chem. 2021, 7(2), 26-32. doi: 10.11648/j.ajhc.20210702.12

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AMA Style

Sayed Abd El-moneim Ahmed Altaweel, Ahmed Abdelhameed Khames, Abu-Bakr Abdelhady Mohamed El-Adasy, Abdallah Mahmoud Ahmed Hassane, Abdel-Haleem Mostafa Hussein. 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. Am J Heterocycl Chem. 2021;7(2):26-32. doi: 10.11648/j.ajhc.20210702.12

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@article{10.11648/j.ajhc.20210702.12,
  author = {Sayed Abd El-moneim Ahmed Altaweel and Ahmed Abdelhameed Khames and Abu-Bakr Abdelhady Mohamed El-Adasy and Abdallah Mahmoud Ahmed Hassane and Abdel-Haleem Mostafa Hussein},
  title = {3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {7},
  number = {2},
  pages = {26-32},
  doi = {10.11648/j.ajhc.20210702.12},
  url = {https://doi.org/10.11648/j.ajhc.20210702.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20210702.12},
  abstract = {In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.},
 year = {2021}
}

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TY  - JOUR
T1  - 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives
AU  - Sayed Abd El-moneim Ahmed Altaweel
AU  - Ahmed Abdelhameed Khames
AU  - Abu-Bakr Abdelhady Mohamed El-Adasy
AU  - Abdallah Mahmoud Ahmed Hassane
AU  - Abdel-Haleem Mostafa Hussein
Y1  - 2021/07/15
PY  - 2021
N1  - https://doi.org/10.11648/j.ajhc.20210702.12
DO  - 10.11648/j.ajhc.20210702.12
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 26
EP  - 32
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20210702.12
AB  - In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.
VL  - 7
IS  - 2
ER  -

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Author Information

Sayed Abd El-moneim Ahmed Altaweel

Chemistry Department, Faculty of Science, Al-Azhar University, Assuit, Egypt
Ahmed Abdelhameed Khames

Chemistry Department, Faculty of Science, Al-Azhar University, Assuit, Egypt
Abu-Bakr Abdelhady Mohamed El-Adasy

Chemistry Department, Faculty of Science, Al-Azhar University, Assuit, Egypt
Abdallah Mahmoud Ahmed Hassane

Botany and Microbiology Department, Faculty of Science, Al-Azhar University, Assiut, Egypt
Abdel-Haleem Mostafa Hussein

Chemistry Department, Faculty of Science, Al-Azhar University, Assuit, Egypt

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Sayed Abd El-moneim Ahmed Altaweel, Ahmed Abdelhameed Khames, Abu-Bakr Abdelhady Mohamed El-Adasy, Abdallah Mahmoud Ahmed Hassane, Abdel-Haleem Mostafa Hussein. (2021). 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. American Journal of Heterocyclic Chemistry, 7(2), 26-32. https://doi.org/10.11648/j.ajhc.20210702.12

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ACS Style

Sayed Abd El-moneim Ahmed Altaweel; Ahmed Abdelhameed Khames; Abu-Bakr Abdelhady Mohamed El-Adasy; Abdallah Mahmoud Ahmed Hassane; Abdel-Haleem Mostafa Hussein. 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. Am. J. Heterocycl. Chem. 2021, 7(2), 26-32. doi: 10.11648/j.ajhc.20210702.12

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AMA Style

Sayed Abd El-moneim Ahmed Altaweel, Ahmed Abdelhameed Khames, Abu-Bakr Abdelhady Mohamed El-Adasy, Abdallah Mahmoud Ahmed Hassane, Abdel-Haleem Mostafa Hussein. 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives. Am J Heterocycl Chem. 2021;7(2):26-32. doi: 10.11648/j.ajhc.20210702.12

Copy | Download

@article{10.11648/j.ajhc.20210702.12,
  author = {Sayed Abd El-moneim Ahmed Altaweel and Ahmed Abdelhameed Khames and Abu-Bakr Abdelhady Mohamed El-Adasy and Abdallah Mahmoud Ahmed Hassane and Abdel-Haleem Mostafa Hussein},
  title = {3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {7},
  number = {2},
  pages = {26-32},
  doi = {10.11648/j.ajhc.20210702.12},
  url = {https://doi.org/10.11648/j.ajhc.20210702.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20210702.12},
  abstract = {In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - 3-Oxobutanamides in Heterocyclic Synthesis: Synthesis, Antimicrobial and Antioxidant Activity of Pyridine, Thiophene, Diazepine and Thiazole Derivatives
AU  - Sayed Abd El-moneim Ahmed Altaweel
AU  - Ahmed Abdelhameed Khames
AU  - Abu-Bakr Abdelhady Mohamed El-Adasy
AU  - Abdallah Mahmoud Ahmed Hassane
AU  - Abdel-Haleem Mostafa Hussein
Y1  - 2021/07/15
PY  - 2021
N1  - https://doi.org/10.11648/j.ajhc.20210702.12
DO  - 10.11648/j.ajhc.20210702.12
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 26
EP  - 32
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20210702.12
AB  - In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.
VL  - 7
IS  - 2
ER  -

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