2-amino-7-methyl-5-oxo-4-phenyl-4,6-dihydropyrano[3,2-c]pyridine-3-carbonitrile synthesis
- Product Name:2-amino-7-methyl-5-oxo-4-phenyl-4,6-dihydropyrano[3,2-c]pyridine-3-carbonitrile
- CAS Number:193887-94-4
- Molecular formula:C16H13N3O2
- Molecular Weight:279.29
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Yield:193887-94-4 98%
Reaction Conditions:
with sodium acetate in ethanol; for 1 h;Catalytic behavior;Reflux;Reagent/catalyst;Solvent;
Steps:
General procedure for preparation of functionalized pyrano[3,2-c]pyridines
Aldehyde 1 (3 mmol), malononitrile (3 mmol), 4-hydroxy-6-methylpyridin-2(1H)-one (3 mmol) and AcONa (0.3 mmol) were refluxed in 5 mL of ethanol for 1 h. After the reaction was finished, the solid was filtered, washed with cold ethanol and dried to isolate pure substituted 2-amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles 2a-i. 2-Amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile (2a) White solid; yield 0.82 g, (98 %); m.p.: 280-282 °C [lit. m.p.: 279-282 °C (Baghbanian et al. 2014)]; 1H NMR (300 MHz, DMSO-d6): δ 2.16 (s, 3H, CH3),4.31 (s, 1H, CH), 5.89 (s, 1H, CH), 7.00 (s, 2H, NH2), 7.14-7.22 (m, 3H, Ar), 7.27-7.31 (m, 2H, Ar), 11.52 (s, 1H, NH).
References:
Elinson, Michail N.;Ryzhkov, Fedor V.;Vereshchagin, Anatoly N.;Goloveshkin, Alexander S.;Bushmarinov, Ivan S.;Egorov, Mikhail P. [Research on Chemical Intermediates,2018,vol. 44,# 5,p. 3199 - 3209]
