METHYL 6-AMINO-5-CYANO-2-(2-METHOXY-2-OXOETHYL)-4-(4-METHOXYPHENYL)-4H-PYRAN-3-CARBOXYLATE synthesis
- Product Name:METHYL 6-AMINO-5-CYANO-2-(2-METHOXY-2-OXOETHYL)-4-(4-METHOXYPHENYL)-4H-PYRAN-3-CARBOXYLATE
- CAS Number:354554-29-3
- Molecular formula:C18H18N2O6
- Molecular Weight:358.35
1830-54-2
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354554-29-3
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Yield:354554-29-3 73%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in ethanol at 20; for 4 h;Reagent/catalyst;Solvent;Temperature;
Steps:
Synthesis of 4-phenyl-4H-pyran derivatives 4a-4i and 7a-7k (general procedure).
A mixture of aldehyde 1a-1i or 5a-5k (4 mmol), malononitrile (4 mmol), dimethyl 3-oxo-1,5-pentanedioate or methyl/ethyl 3-oxo-3-arylpropanoate (4 mmol), respectively, and DIPEA (6 mmol) in EtOH (20 mL) was stirred at room temperature. The reaction progress was monitored by TLC. After completion of the reaction, the solid material that formed was collected by filtration and recrystallized from EtOH to obtain the desired product. Methyl 6-amino-5-cyano-2-(2-methoxy-2-oxoethyl)-4-(4-methoxyphenyl)-4H-pyran-3-carboxylate (4a). Yield 73%, mp 154-156°C (157-159°C [26]). IR spectrum, ν, cm-1: 3415 (NH2), 3326 (NH2), 2187 (CN), 1757 (C=O), 1699 (C=O), 1676 (C=Carom), 1641, 1603, 1439, 1415, 1362, 1329, 1275, 1167, 1120, 1068, 861 (δC-Harom), 773. 1H NMR spectrum (CDCl3), δ, ppm: 7.20 d (2Harom, J 8.4 Hz), 6.87 d (2Harom, J 8.4 Hz), 4.52 s (2H, NH2), 4.45 s (1H, CH), 3.94 d (1H, CH2, J 16.8 Hz), 3.80 s (3H, CH3), 3.77 br.s (4H, CH3, CH2), 3.61 s (3H, CH3). 13C NMR spectrum (CDCl3), δ, ppm: 168.87 (CO), 165.83 (CH2CO), 158.82, 157.15, 152.74, 135.60, 128.54, 118.64, 114.13, 110.55, 63.02, 55.25 (OCH3), 52.50 (COOCH3), 52.00 (CH2COOCH3), 37.84 (CH), 37.82 (CH2). Mass spectrum: m/z 381.2 [M + Na]+. Found, %: C 60.38; H 5.02; N 7.85. C18H18N2O6. Calculated, %: C 60.33; H 5.06; N 7.82.
References:
Li, Jun;Li, Jie;Hu, Shi-yu;Chen, Ye;Liu, Ju [Russian Journal of Organic Chemistry,2019,vol. 55,# 11,p. 1791 - 1799][Zh. Org. Khim.]
1830-54-2
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