Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone

Molou Kouassi Yves Guillaume; Timotou Adeyole; Coulibaly Souleymane; Camara Tchambaga Etienne; Kablan Ahmont Landry Claude; Coulibali Siomenan; Sissouma Drissa

doi:doi:10.11648/j.mc.20221004.11

Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone

Molou Kouassi Yves Guillaume, Timotou Adeyole, Coulibaly Souleymane, Camara Tchambaga Etienne, Kablan Ahmont Landry Claude, Coulibali Siomenan, Sissouma Drissa

Published in Modern Chemistry (Volume 10, Issue 4)

Received: 6 October 2022 Accepted: 25 October 2022 Published: 4 November 2022

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Abstract

Heterocycles containing pyrimidine and pyridine moieties are of great interest because they represent an important class of natural products such as nucleic acid, cytosine, and thymine. In addition, structural thiazole and benzimidazole subunits are present in various synthetic compounds, many of them have beneficial biological activities. The combination of these structures could beneficial in the discovery of new bioactive molecules and drugs. In this article, the synthesis of two series of new molecules derived from both pyrimidinothiazole (7a, 7b) and pyrimidinobenzimidazole carboxylic acids (9a-c) was presented. Structurally, these compounds are 4-quinolone analogs, which also possess medicinal properties. These compounds were synthesized by first developing ethyl pyrimidinothiazoles carboxylate (6a, 6b) and pyrimidinobenzimidazoles N-ethyl carboxylate (8a-c). Ethyl pyrimidinothiazoles carboxylate (6a, 6b) were synthesized by condensing ethyl ethoxymethylenemalonate with 2-amino-1,3-thiazoles (2a-b) at ethanol reflux. Pyrimidinobenzimidazoles carboxylate N-ethyl (8a-c) were obtained by an interaction between 2-aminobenzimidazoles (4a-c) and ethyl ethoxymethylenemalonate (5) followed by N-alkylation by the action of ethyl iodide in the presence of potassium carbonate. Obtained esters (6a, 6b) and (8a-c) were converted to the corresponding acids (7a, 7b) and (9a-c) by saponification with sodium hydroxide followed by neutralization with acetic acid. The structure of the compounds was confirmed by spectroscopic analysis of ¹H, ¹³C-NMR and mass spectrometry.

Published in	Modern Chemistry (Volume 10, Issue 4)
DOI	10.11648/j.mc.20221004.11
Page(s)	106-112
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

4-Quinolones, Pyrimidinobenzimidazole Carboxylic Acid, Pyrimidino-Benzimidazoles N-ethyl Carboxylate, N-alkylation

References

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Molou Kouassi Yves Guillaume, Timotou Adeyole, Coulibaly Souleymane, Camara Tchambaga Etienne, Kablan Ahmont Landry Claude, et al. (2022). Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Modern Chemistry, 10(4), 106-112. https://doi.org/10.11648/j.mc.20221004.11

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ACS Style

Molou Kouassi Yves Guillaume; Timotou Adeyole; Coulibaly Souleymane; Camara Tchambaga Etienne; Kablan Ahmont Landry Claude, et al. Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Mod. Chem. 2022, 10(4), 106-112. doi: 10.11648/j.mc.20221004.11

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AMA Style

Molou Kouassi Yves Guillaume, Timotou Adeyole, Coulibaly Souleymane, Camara Tchambaga Etienne, Kablan Ahmont Landry Claude, et al. Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Mod Chem. 2022;10(4):106-112. doi: 10.11648/j.mc.20221004.11

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@article{10.11648/j.mc.20221004.11,
  author = {Molou Kouassi Yves Guillaume and Timotou Adeyole and Coulibaly Souleymane and Camara Tchambaga Etienne and Kablan Ahmont Landry Claude and Coulibali Siomenan and Sissouma Drissa},
  title = {Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone},
  journal = {Modern Chemistry},
  volume = {10},
  number = {4},
  pages = {106-112},
  doi = {10.11648/j.mc.20221004.11},
  url = {https://doi.org/10.11648/j.mc.20221004.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221004.11},
  abstract = {Heterocycles containing pyrimidine and pyridine moieties are of great interest because they represent an important class of natural products such as nucleic acid, cytosine, and thymine. In addition, structural thiazole and benzimidazole subunits are present in various synthetic compounds, many of them have beneficial biological activities. The combination of these structures could beneficial in the discovery of new bioactive molecules and drugs. In this article, the synthesis of two series of new molecules derived from both pyrimidinothiazole (7a, 7b) and pyrimidinobenzimidazole carboxylic acids (9a-c) was presented. Structurally, these compounds are 4-quinolone analogs, which also possess medicinal properties. These compounds were synthesized by first developing ethyl pyrimidinothiazoles carboxylate (6a, 6b) and pyrimidinobenzimidazoles N-ethyl carboxylate (8a-c). Ethyl pyrimidinothiazoles carboxylate (6a, 6b) were synthesized by condensing ethyl ethoxymethylenemalonate with 2-amino-1,3-thiazoles (2a-b) at ethanol reflux. Pyrimidinobenzimidazoles carboxylate N-ethyl (8a-c) were obtained by an interaction between 2-aminobenzimidazoles (4a-c) and ethyl ethoxymethylenemalonate (5) followed by N-alkylation by the action of ethyl iodide in the presence of potassium carbonate. Obtained esters (6a, 6b) and (8a-c) were converted to the corresponding acids (7a, 7b) and (9a-c) by saponification with sodium hydroxide followed by neutralization with acetic acid. The structure of the compounds was confirmed by spectroscopic analysis of 1H, 13C-NMR and mass spectrometry.},
 year = {2022}
}

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TY  - JOUR
T1  - Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone
AU  - Molou Kouassi Yves Guillaume
AU  - Timotou Adeyole
AU  - Coulibaly Souleymane
AU  - Camara Tchambaga Etienne
AU  - Kablan Ahmont Landry Claude
AU  - Coulibali Siomenan
AU  - Sissouma Drissa
Y1  - 2022/11/04
PY  - 2022
N1  - https://doi.org/10.11648/j.mc.20221004.11
DO  - 10.11648/j.mc.20221004.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 106
EP  - 112
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20221004.11
AB  - Heterocycles containing pyrimidine and pyridine moieties are of great interest because they represent an important class of natural products such as nucleic acid, cytosine, and thymine. In addition, structural thiazole and benzimidazole subunits are present in various synthetic compounds, many of them have beneficial biological activities. The combination of these structures could beneficial in the discovery of new bioactive molecules and drugs. In this article, the synthesis of two series of new molecules derived from both pyrimidinothiazole (7a, 7b) and pyrimidinobenzimidazole carboxylic acids (9a-c) was presented. Structurally, these compounds are 4-quinolone analogs, which also possess medicinal properties. These compounds were synthesized by first developing ethyl pyrimidinothiazoles carboxylate (6a, 6b) and pyrimidinobenzimidazoles N-ethyl carboxylate (8a-c). Ethyl pyrimidinothiazoles carboxylate (6a, 6b) were synthesized by condensing ethyl ethoxymethylenemalonate with 2-amino-1,3-thiazoles (2a-b) at ethanol reflux. Pyrimidinobenzimidazoles carboxylate N-ethyl (8a-c) were obtained by an interaction between 2-aminobenzimidazoles (4a-c) and ethyl ethoxymethylenemalonate (5) followed by N-alkylation by the action of ethyl iodide in the presence of potassium carbonate. Obtained esters (6a, 6b) and (8a-c) were converted to the corresponding acids (7a, 7b) and (9a-c) by saponification with sodium hydroxide followed by neutralization with acetic acid. The structure of the compounds was confirmed by spectroscopic analysis of 1H, 13C-NMR and mass spectrometry.
VL  - 10
IS  - 4
ER  -

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Author Information

Molou Kouassi Yves Guillaume

Ecole Normale Superieure, Abidjan, C?te d’Ivoire
Timotou Adeyole

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire
Coulibaly Souleymane

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire
Camara Tchambaga Etienne

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire
Kablan Ahmont Landry Claude

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire
Coulibali Siomenan

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire
Sissouma Drissa

Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, University Felix Houphouet Boigny, Abidjan, C?te d’Ivoire

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APA Style

Molou Kouassi Yves Guillaume, Timotou Adeyole, Coulibaly Souleymane, Camara Tchambaga Etienne, Kablan Ahmont Landry Claude, et al. (2022). Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Modern Chemistry, 10(4), 106-112. https://doi.org/10.11648/j.mc.20221004.11

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ACS Style

Molou Kouassi Yves Guillaume; Timotou Adeyole; Coulibaly Souleymane; Camara Tchambaga Etienne; Kablan Ahmont Landry Claude, et al. Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Mod. Chem. 2022, 10(4), 106-112. doi: 10.11648/j.mc.20221004.11

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AMA Style

Molou Kouassi Yves Guillaume, Timotou Adeyole, Coulibaly Souleymane, Camara Tchambaga Etienne, Kablan Ahmont Landry Claude, et al. Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone. Mod Chem. 2022;10(4):106-112. doi: 10.11648/j.mc.20221004.11

Copy | Download

@article{10.11648/j.mc.20221004.11,
  author = {Molou Kouassi Yves Guillaume and Timotou Adeyole and Coulibaly Souleymane and Camara Tchambaga Etienne and Kablan Ahmont Landry Claude and Coulibali Siomenan and Sissouma Drissa},
  title = {Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone},
  journal = {Modern Chemistry},
  volume = {10},
  number = {4},
  pages = {106-112},
  doi = {10.11648/j.mc.20221004.11},
  url = {https://doi.org/10.11648/j.mc.20221004.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221004.11},
  abstract = {Heterocycles containing pyrimidine and pyridine moieties are of great interest because they represent an important class of natural products such as nucleic acid, cytosine, and thymine. In addition, structural thiazole and benzimidazole subunits are present in various synthetic compounds, many of them have beneficial biological activities. The combination of these structures could beneficial in the discovery of new bioactive molecules and drugs. In this article, the synthesis of two series of new molecules derived from both pyrimidinothiazole (7a, 7b) and pyrimidinobenzimidazole carboxylic acids (9a-c) was presented. Structurally, these compounds are 4-quinolone analogs, which also possess medicinal properties. These compounds were synthesized by first developing ethyl pyrimidinothiazoles carboxylate (6a, 6b) and pyrimidinobenzimidazoles N-ethyl carboxylate (8a-c). Ethyl pyrimidinothiazoles carboxylate (6a, 6b) were synthesized by condensing ethyl ethoxymethylenemalonate with 2-amino-1,3-thiazoles (2a-b) at ethanol reflux. Pyrimidinobenzimidazoles carboxylate N-ethyl (8a-c) were obtained by an interaction between 2-aminobenzimidazoles (4a-c) and ethyl ethoxymethylenemalonate (5) followed by N-alkylation by the action of ethyl iodide in the presence of potassium carbonate. Obtained esters (6a, 6b) and (8a-c) were converted to the corresponding acids (7a, 7b) and (9a-c) by saponification with sodium hydroxide followed by neutralization with acetic acid. The structure of the compounds was confirmed by spectroscopic analysis of 1H, 13C-NMR and mass spectrometry.},
 year = {2022}
}

Copy | Download

TY  - JOUR
T1  - Design, Synthesis of Pyrimidinothiazoles and Pyrimidinobenzimidazoles N-ethyl Carboxylic Acid Derivatives Analogs of 4-Quinolone
AU  - Molou Kouassi Yves Guillaume
AU  - Timotou Adeyole
AU  - Coulibaly Souleymane
AU  - Camara Tchambaga Etienne
AU  - Kablan Ahmont Landry Claude
AU  - Coulibali Siomenan
AU  - Sissouma Drissa
Y1  - 2022/11/04
PY  - 2022
N1  - https://doi.org/10.11648/j.mc.20221004.11
DO  - 10.11648/j.mc.20221004.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 106
EP  - 112
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20221004.11
AB  - Heterocycles containing pyrimidine and pyridine moieties are of great interest because they represent an important class of natural products such as nucleic acid, cytosine, and thymine. In addition, structural thiazole and benzimidazole subunits are present in various synthetic compounds, many of them have beneficial biological activities. The combination of these structures could beneficial in the discovery of new bioactive molecules and drugs. In this article, the synthesis of two series of new molecules derived from both pyrimidinothiazole (7a, 7b) and pyrimidinobenzimidazole carboxylic acids (9a-c) was presented. Structurally, these compounds are 4-quinolone analogs, which also possess medicinal properties. These compounds were synthesized by first developing ethyl pyrimidinothiazoles carboxylate (6a, 6b) and pyrimidinobenzimidazoles N-ethyl carboxylate (8a-c). Ethyl pyrimidinothiazoles carboxylate (6a, 6b) were synthesized by condensing ethyl ethoxymethylenemalonate with 2-amino-1,3-thiazoles (2a-b) at ethanol reflux. Pyrimidinobenzimidazoles carboxylate N-ethyl (8a-c) were obtained by an interaction between 2-aminobenzimidazoles (4a-c) and ethyl ethoxymethylenemalonate (5) followed by N-alkylation by the action of ethyl iodide in the presence of potassium carbonate. Obtained esters (6a, 6b) and (8a-c) were converted to the corresponding acids (7a, 7b) and (9a-c) by saponification with sodium hydroxide followed by neutralization with acetic acid. The structure of the compounds was confirmed by spectroscopic analysis of 1H, 13C-NMR and mass spectrometry.
VL  - 10
IS  - 4
ER  -

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