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Open AccessArticle

A Novel Synthesis of Highly Functionalized Pyridines by a One-Pot, Three-Component Tandem Reaction of Aldehydes, Malononitrile and N-Alkyl-2-cyanoacetamides under Microwave Irradiation

1
Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
2
Chemistry Department, Faculty of Sciences-Al Faisaliah, King Abdulaziz University, Jeddah 21493, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(3), 619; https://doi.org/10.3390/molecules23030619
Received: 9 February 2018 / Revised: 24 February 2018 / Accepted: 4 March 2018 / Published: 9 March 2018
(This article belongs to the Section Organic Chemistry)
A convenient, fast and environmentally benign procedure for the synthesis of a new series of highly functionalized N-alkylated pyridines as privileged medicinal scaffolds was developed via a unique three-component reaction of easily available aromatic as well as heteroaromatic aldehydes, N-alkyl-2-cyanoacetamides and malononitrile in EtOH in the presence of K2CO3 as a base promoter under microwave irradiation. The presented tandem process is presumed to proceed via Knoevenagel condensation, Michael addition, intramolecular cyclization, autoxidation and subsequent aromatization. Particularly valuable features of this protocol, including high product yields, mild conditions, atom-efficiency, simple execution, short reaction times and easy purification make it a highly efficient and promising synthetic strategy to prepare substituted pyridine nuclei. The proposed mechanism of this novel one-pot reaction and structure elucidation of the products are discussed. View Full-Text
Keywords: synthesis; one-pot; three-component; tandem reaction; microwave irradiation; pyridines synthesis; one-pot; three-component; tandem reaction; microwave irradiation; pyridines
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MDPI and ACS Style

Mekheimer, R.A.; Al-Sheikh, M.A.; Medrasi, H.Y.; Alsofyani, N.H.H. A Novel Synthesis of Highly Functionalized Pyridines by a One-Pot, Three-Component Tandem Reaction of Aldehydes, Malononitrile and N-Alkyl-2-cyanoacetamides under Microwave Irradiation. Molecules 2018, 23, 619.

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