ChemicalBook CAS DataBase List ethyl 5-amino-4-oxo-3-phenyl-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxyla te

ethyl 5-amino-4-oxo-3-phenyl-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxyla te synthesis

5synthesis methods

Product Name:ethyl 5-amino-4-oxo-3-phenyl-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxyla te
CAS Number:123542-47-2
Molecular formula:C15H13N3O3S
Molecular Weight:315.35

ethyl 5-cyano-4-methyl-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate

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ethyl 5-amino-4-oxo-3-phenyl-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxyla te

123542-47-2
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Yield:123542-47-2 84%

Reaction Conditions:

with sulphur;triethylamine in ethanol at 70; for 0.0833333 h;Microwave irradiation;

Steps:

Ethyl 5-amino-3, 4-dihydro-4-oxo-3-phenyl thieno[3,4-d]pyridazine-1-carboxylate (10)

To a solution of (1a, 0.01 mol) in ethanol(20 mL); elemental sulphur (0.01 mol) and a catalytic amount of triethylamine were added. The reaction mixture was heated under reflux in amicrowave labStation at 70 C for 5 min the solid product formed cooling at room temperature and collected by filtration and recrystallizationfrom ethanol. Compound (10) obtained as yellow crystals fromethanol, yield 84%; m.p. 199-201 C (Lit. m.p. 200 C) [53]. IR, cm 1,λmax = 3390, 3200 (NH2), 1725, 1710 (CO). 1H NMR (300 MHz,DMSO-d6): δ (ppm) = 1.31 (t, 3H, J = 5.6 Hz, CH3); 4.33 (q, 2H, J = 7.2Hz, CH2); 7.12 (s, 1H, CH- thienyl), 7.38-7.40 (m, 1H, ArH), 7.40-7.53(m, 4H, Ar-H); 7.65 (s, 2H, NH2). 13C NMR (100 MHz, DMSO-d6): δ(ppm) = 14.54; 61.81; 103.82; 104.39; 126.56; 126.81; 127.90; 128.97;133.23; 141.21; 158.80; 162.92; 163.69.

References:

Hassan Nazmy, Maiiada;Ahmed Mekheimer, Ramadan;Shoman, Mai E.;Abo-Elsebaa, Mohamed;Abd-Elmonem, Mohamed;Usef Sadek, Kamal [Bioorganic Chemistry,2022,vol. 122,art. no. 105740]

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