Boric acid catalyzed convenient synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines in aqueous media

Tetrahedron Letters

Volumn 51, Issue 9, 2010, Pages 1309-1312

  Shinde, Pravin V ^a   Sonar, Swapnil S ^a   Shingate, Bapurao B ^a   Shingare, Murlidhar S ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Aldehyde; Aqueous media; Boric acid; Malononitrile; Thiophenol; Ultrasonication

Indexed keywords

2 AMINO 3,5 DICARBONITRILE 6 THIO PYRIDINE DERIVATIVE; ALDEHYDE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BORIC ACID; MALONONITRILE; PYRIDINE DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ULTRASOUND;

EID: 74749089821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.146     Document Type: Article

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44. Typical experimental procedure:Conventional method: A mixture of benzaldehyde 1a (106 mg, 1 mmol), malononitrile 2 (132 mg, 2 mmol), thiophenol 3a (110 mg, 1 mmol) and boric acid (15 mol %) in water (5 mL) was stirred at 80 °C in the presence of CTAB (10 mol %) for 40 min. Reaction progress was monitored by TLC (ethyl acetate/n-hexane, 1:7). After completion of reaction, the solid product was collected by simple filtration and washed with water. The crude product (4a) was recrystallized from ethanol to obtain pure product.Ultrasound method: A mixture of benzaldehyde 1a (106 mg, 1 mmol), malononitrile 2 (132 mg, 2 mmol), thiophenol 3a (110 mg, 1 mmol) and boric acid (15 mol %) in water (5 mL) was subjected to ultrasound irradiation at 80 °C in the presence of CTAB (10 mol %) for 10 min After completion of reaction, as monitored by TLC (ethyl acetate/n-hexane, 1:7) the solid product was collected by simple filtration and washed with water. The crude product (4a) was purified by recrystallization from ethanol.
45. -1): ν 3473, 3348, 3290, 2958, 2212, 1625, 1533, 1281, 1020, 756; ES-MS: 390.04 (M+1).