Green Synthesis of Novel Pyridines via One-Pot Multicomponent Reaction and Their Anti-Inflammatory Evaluation

Hany M Abd El-Lateef; Antar A Abdelhamid; Mai M Khalaf; Mohamed Gouda; Nadia A A Elkanzi; Hemdan El-Shamy; Ali M Ali

doi:10.1021/acsomega.3c00066

Green Synthesis of Novel Pyridines via One-Pot Multicomponent Reaction and Their Anti-Inflammatory Evaluation

ACS Omega. 2023 Mar 16;8(12):11326-11334. doi: 10.1021/acsomega.3c00066. eCollection 2023 Mar 28.

Authors

Hany M Abd El-Lateef^{1

2}, Antar A Abdelhamid^{2

3}, Mai M Khalaf^{1

2}, Mohamed Gouda¹, Nadia A A Elkanzi^{4

5}, Hemdan El-Shamy⁶, Ali M Ali²

Affiliations

¹ Department of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi Arabia.
² Department of Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt.
³ Department of Chemistry, Faculty of Science, Albaha University, P.O. Box 1988, Al Baha Saudi Arabia.
⁴ Department of Chemistry, College of Science, Jouf University, P.O. Box 2014, Sakaka, Saudi Arabia.
⁵ Department of Chemistry, Faculty of Science, Aswan University, P.O. Box 81528, Aswan, Egypt.
⁶ Deanship of Student Affairs, King Faisal University, P.O. Box 380, Al-Ahsa 31982, Saudi Arabia.

Abstract

A functional and environmentally green procedure for the design of novel pyridine 5a-h and 7a-d derivatives through two pathways is presented. The first pathway is via a one-pot, four-component reaction of p-formylphenyl-4-toluenesulfonate (1), ethyl cyanoacetate (2), acetophenone derivatives 3a-h or acetyl derivatives 6a-d, and ammonium acetate (4) under microwave irradiation in ethanol. The advantages of this method are an excellent yield (82%-94%), pure products, a short reaction time (2-7 min), and low-cost processing. The second pathway was obtained by the traditional method with treatment of the same mixture under refluxing in ethanol, which afforded the same products, 5a-h and 7a-d, in less yield (71%-88%) and over a longer reaction time (6-9 h). The constructions of the novel compounds were articulated via spectral and elemental analysis. Overall, the compounds have been designed, synthesized, and studied for their in vitro anti-inflammatory activity using diclofenac as a reference drug (5 mg/kg). The most potent four compounds, 5a, 5f, 5g, and 5h, showed promising anti-inflammatory activity.