Improved One-Pot, Four-Component Strategy to Access ­Functionalized Dihydropyridines by Using 4-(N,N-Dimethylamino)pyridine as a Catalyst

Rathinam Ramesh; Mani Arivazhagan; Jan Grzegorz Malecki; Appaswami Lalitha

doi:10.1055/s-0037-1609579

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(14): 1897-1901
DOI: 10.1055/s-0037-1609579

letter

Improved One-Pot, Four-Component Strategy to Access Functionalized Dihydropyridines by Using 4-(N,N-Dimethylamino)pyridine as a Catalyst

Rathinam Ramesh

^aDepartment of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem-636011, Tamil Nadu, India eMail: lalitha253@periyaruniversity.ac.in

,

Mani Arivazhagan

^aDepartment of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem-636011, Tamil Nadu, India eMail: lalitha253@periyaruniversity.ac.in

,

Jan Grzegorz Malecki

^bDepartment of Crystallography, University of Silesia, Szkolna 9, 40-007 Katowice, Poland

,

Appaswami Lalitha*

^aDepartment of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem-636011, Tamil Nadu, India eMail: lalitha253@periyaruniversity.ac.in

› Institutsangaben

Abstract

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Abstract

A convenient strategy has been developed for the synthesis of structurally diverse novel 1,4-dihydropyridine frameworks bearing a 3-nitrophenyl moiety through a one-pot, four-component reaction with 4-(N,N-dimethylamino)pyridine as a catalyst at room temperature. This tandem process proceeds more effectively than previous catalytic processes.

Key words

dimethylaminopyridine - nitrophenyldihydropyridines - multicomponent reactions - nitriles - amines - organocatalysis

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Referenzen

References and Notes

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31 Dimethyl 6-Amino-5-cyano-4-(3-nitrophenyl)-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate (5l); Typical Procedure 3-Nitrobenzaldehyde (2.5 mmol), malononitrile (2.5 mmol), and DMAP (10 mol%) were dissolved in EtOH (5 mL), and the mixture was stirred at r.t. for 2 min. A solution of DMAD (2.5 mmol) and aniline (2.5 mmol) in EtOH (5 mL) was added slowly, and the resulting mixture was stirred at r.t. for 20 min. When the reaction was complete (TLC; EtOAc–hexane), the solid that formed was collected by filtration, dried, and crystallized from EtOH.
32 Dimethyl 6-Amino-5-cyano-1-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-2,3-dicarboxylate (5a) Yellow crystals; yield: 1118 mg (96%); mp 194–196 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 3.40 (s, 3 H, COOCH₃), 3.55 (s, 3 H, COOCH₃), 3.83 (s, 3 H, OCH₃), 4.71 (s, 1 H, CH), 5.81 (s, 2 H, NH₂), 7.05 (d, J = 8.0 Hz, 2 H, ArH), 7.25 (d, J = 8.0 Hz, 2 H, ArH), 7.79 (d, J = 8.0 Hz, 2 H, ArH), 8.16 (d, J = 8.0 Hz, 2 H, ArH). ¹³C NMR (100 MHz, DMSO-d₆ ): δ = 38.2, 52.0, 52.4, 55.4, 58.4, 103.3, 114.7, 120.6, 121.0, 122.1, 127.2, 130.5, 131.3, 133.5, 142.8, 147.6, 148.0, 151.4, 160.0, 162.7, 164.7.
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Zusatzmaterial

Improved One-Pot, Four-Component Strategy to Access ­Functionalized Dihydropyridines by Using 4-(N,N-Dimethylamino)pyridine as a Catalyst

Improved One-Pot, Four-Component Strategy to Access Functionalized Dihydropyridines by Using 4-(N,N-Dimethylamino)pyridine as a Catalyst