1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone

Aryan Younessi ^1* and Gennady D. Krapivin ²

¹ Research Laboratory of Furan Chemistry and ² Department of Organic Chemistry, Kuban State University of Technology, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
E-mail: [email protected], [email protected]

Received: 31 March 2003 / Accepted 18 June 2003 / Published 22 June 2003

1,4-Dihydropyridines are of interest because some of them exhibit various kinds of pharmaceutical activity [1-3]. So in the course of our study we have synthesized novel derivatives of 1,4-dihydropyridine based on the reactions of furaldehydes with acetylacetone.

A mixture of acetylacetone (5.0 g, 30 mmol), furfural (2.4 g, 25 mmol) and CH₃COONH₄ (1.25 g, 16 mmol) in 20 mL of ethanol was refluxed for 5 h (the reaction duration was monitored with TLC) and left overnight at room temperature. Then solvent was evaporated, residue was washed with water, dried and recrystallized from ethyl acetate - hexane mixture to yield 3.19 g, 77 % of titled compound as pale yellow crystals. 

Mp: 159-160 °C.

IR (KBr): 3300, 3230, 1675, 1665 cm^-1.

¹H NMR (acetone-d₆, 60 MHz, ppm): 2.23 (s, 12H, 4 CH₃), 5.15 (s, 1H, H_A), 5.85 (d, J_3,4 = 3.2, 3-H_Fur), 6.13 (d, J_4,5 = 1.8, 4-H_Fur), 7.20 (d, J_3,5 = 0.9, 5-H_Fur), 7.97 (s, 1H, NH).

Anal. calc. for C₁₅H₁₇NO₃: C 69.48, H 6.61, N 5.40; Found: C 69.79, H 6.44, N 5.57. 

References and Notes

1. Schleifer, K-J. J. Med. Chem. 1999, 42, 2204.

2. Visentin, S.; Amiel, P.; Frittero, R. et al. J. Med. Chem. 1999, 42, 1422.

3. Jiang, J-L.; Li, A-H.; Jang, S-Y. et al. J. Med. Chem. 1999, 42, 3055.

Sample availability: available from the authors. 

© 2003 MDPI. All rights reserved.