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Volumn , Issue 12, 2009, Pages 2020-2022

Synthesis of highly substituted pyridines via a one-pot, three-component cascade reaction of malononitrile with aldehydes and S-alkylisothiouronium salts in water

(4) Wang, Zhong Qing a Ge, Ze Mei a Cheng, Tie Ming a Li, Run Tao a

a PEKING UNIVERSITY HEALTH SCIENCE CENTER (China)

Author keywords

2 amino 4 aryl(alkyl) 6 sulfanyl pyridine 3,5 dicarbonitrile; Green chemistry; Multicomponent reactions; S alkylisothiouronium salts; Thiols

Indexed keywords

2 AMINO 4 PHENYL 6 (METHLSULFANYL)PYRIDINE 2,5 DICARBONITRILE; ALDEHYDE; ALDEHYDE DERIVATIVE; MALONONITRILE; PYRIDINE DERIVATIVE; THIOL; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTALLIZATION; FILTRATION; ONE POT SYNTHESIS; REACTION TIME; REACTOR CASCADE; SUBSTITUTION REACTION;

EID: 67749122289 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217529 Document Type: Article

Times cited : (18)

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- Representative Procedure for the Synthesis of Compound 3a A mixture of benzaldehyde (106 mg, 1 mmol, malononitrile (132 mg, 2 mmol, NaOH (120 mg, 3 mmol, and SDS (29 mg, 0.1 mmol) in H2O (10 mL) was stirred for 10 min at r.t. The S-methylisothiouronium sulfate (139 mg, 1 mmol) was added. The reaction mixture was further stirred for 50 min until the completion of the reaction (monitored by TLC, The reaction mixture was then filtered and washed with H2O to give the crude solid, which was recrystallized from MeCN to furnish the crystals of 2-amino-4-phenyl-6- methylsulfanylpyridine-3,5-dicarbonitrile (238 mg, 89, mp 295-296 °C. 1H NMR (300 MHz, CDCl3, δ, 2.59 (s, 3 H, SCH 3, 5.67 (br s, 2 H, NH2, 7.50-7.55 (m, 5 H, Ph, 13C NMR 75 MHz, DMSO-d6, δ, 12.79, 85.55, 93.49, 115.31, 115.46, 128.42, 128.71, 130.33, 133.98, 158.17, 159.72, 167.53. Anal. Calcd fo
- 1H NMR and mp which were consistent with the reported data (see Supporting Information).

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