2H-Indol-2-one, 1,3-dihydro-3-(2-pyridinylmethylene)-, (3Z)- synthesis
- Product Name:2H-Indol-2-one, 1,3-dihydro-3-(2-pyridinylmethylene)-, (3Z)-
- CAS Number:187325-53-7
- Molecular formula:C14H10N2O
- Molecular Weight:222.24
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Yield:187325-53-7 79%
Reaction Conditions:
with piperidine in ethanol; for 0.5 h;Reflux;
Steps:
5 4.1.3.1 (Z)-3-(2-Pyridinylmethylidene)-2-oxindole16 (3a)
General procedure: The mixture of 44 2-oxindole 2a (0.1g, 0.0008mol), 84 2-pyridinecarboxaldehyde (0.08g, 0.0008mol) and 85 piperidine (60μL) in 55 ethanol (2mL) was refluxed for 30min. The product 86 3a was obtained after solvent evaporation as single isomer. Brown powder, yield 79% (0.13g). Mp (exp)=185-190°C, mp. 196-198°C (Z isomer)16.dH (400MHz, DMSO-d6): 6.87 (1H, d, J 7.7, CHAr), 6.98 (1H, t, J 7.6, CHAr), 7.28 (t, J 7.6, CHAr), 7.46 (1H, t, J 6.1, CHAr), 7.57 (1H, s, CH=), 7.86 (1H, d, J 7.8, CHAr), 7.94 (1H, t, J 7.6, CHAr), 8.88 (1H, br s, CHAr), 9.00 (1H, d, J 7.6, CHAr), 10.64 (1H, br s, NH); dC (100.6MHz, DMSO-d6): 110.10, 121.71, 121.95, 124.60, 128.39, 128.85, 131.30, 134.14, 137.71, 144.04, 150.13, 153.67, 161.60, 169.77.
References:
Lozinskaya, Natalia A.;Babkov, Denis A.;Zaryanova, Ekaterina V.;Bezsonova, Elena N.;Efremov, Alexander M.;Tsymlyakov, Michael D.;Anikina, Lada V.;Zakharyascheva, Olga Yu.;Borisov, Alexander V.;Perfilova, Valentina N.;Tyurenkov, Ivan N.;Proskurnina, Marina V.;Spasov, Alexander A. [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 9,p. 1804 - 1817]
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