Pyridine-mediated, one-pot, stereoselective synthesis of acyclic enaminones

Tetrahedron Letters

Volumn 52, Issue 31, 2011, Pages 4005-4007

  Ghandi, Mehdi ^a   Jameà, Amir Hossein ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Acyclic enaminones; Ethyl glyoxalate; Phenyl glyoxal

Indexed keywords

4 CHLOROANILINE; AROMATIC AMINE; ENAMINE; ENAMINONE DERIVATIVE; ETHYL GLYOXALATE; GLYOXYLIC ACID; PHENACYL PYRIDINIUM BROMIDE; PHENYL GLYOXAL; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ONE POT SYNTHESIS; STEREOCHEMISTRY; STEREOSELECTIVE SYNTHESIS;

EID: 79959914090     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.112     Document Type: Article

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20. A solution of pyridine (158 mg, 2 mmol) and phenacyl bromide (398 mg, 2 mmol) in EtOAc (5 mL) was stirred at room temperature for 24 h. The resulting white salt was filtered and washed with EtOAc (5 mL) to afford phenacyl pyridinium bromide as a white solid (526 mg, 95%).
21. A mixture of phenacyl pyridinium bromide (556 mg, 2.0 mmol), p-chloroaniline (254 mg, 2 mmol), and ethyl glyoxalate (2 mmol, 50% solution in toluene) was stirred at room temperature for 1 h. The solution was then heated at reflux for 12 h. The solvent was evaporated under reduced pressure and the residue purified by column chromatography over silica gel (eluent: hexane-EtOAc, 10:1) to afford 1.
22. 3: C, 65.56; H, 4.89; N, 4.25. Found: C, 65.58; H, 4.90; N, 4.23.
23. 3: C, 74.75; H, 6.87; N, 4.15. Found: C, 74.70; H, 6.89; N, 4.1713.
24. 2: C, 74.34; H, 5.49; N, 3.47. Found C, 74.30; H, 5.42; N, 3.49.