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. 2018 Dec 14;8(73):41892-41903.
doi: 10.1039/c8ra09155b. eCollection 2018 Dec 12.

Microwave irradiation: a green approach for the synthesis of functionalized N-methyl-1,4-dihydropyridines

M Musawwer Khan  1 , Saigal  1 , Sarfaraz Khan  1 , Sumbulunnisan Shareef  1 , Subash C Sahoo  2
Affiliations

Microwave irradiation: a green approach for the synthesis of functionalized N-methyl-1,4-dihydropyridines

M Musawwer Khan et al. RSC Adv. .

Abstract

An eco-friendly and cost-effective, microwave-assisted green approach has been developed for the synthesis of diverse functionalized N-methyl-1,4-dihydropyridines (1,4-DHPs). This pseudo three-component reaction was carried out between two equivalents of (E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) and one equivalent of aromatic aldehydes under microwave irradiation at 100 °C without catalyst and solvent. Short reaction times, avoidance of toxic solvents or expensive, metallic and corrosive catalysts and no need for column chromatographic purification are among the valuable features of the presented method. Moreover, the "greenness" of the method was evaluated within the ambits of the defined green metrics such as atom economy, carbon efficiency, E-factor, reaction mass efficiency, overall efficiency, process mass intensity and solvent intensity and the method exhibited a good to excellent score.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Some biologically active highly substituted 1,4-DHPs.
Scheme 1
Scheme 1. Synthesis of highly functionalized N-methyl-1,4-dihydropyridines.
Fig. 2
Fig. 2. % yield of reaction vs. reaction temperature for the synthesis of 3a.
Fig. 3
Fig. 3. ORTEP diagram of compound 3n (CCDC 1841358).
Fig. 4
Fig. 4. Unit cell packing of compound 3n.
Scheme 2
Scheme 2. Plausible reaction mechanism for the synthesis of N-methyl-1,4-DHPs.
See this image and copyright information in PMC

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