Construction of a 3-amino-2-pyridone library by ring-closing metathesis of α-amino acrylamide

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 684-687

  Chen, Yihua ^a   Zhang, Huajie ^a   Nan, Fajun ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 2 PYRIDONE; ACRYLAMIDE DERIVATIVE; ALCOHOL; AMINE; AMMONIUM DERIVATIVE; CERIUM; LACTAM DERIVATIVE; NITROGEN; PYRIDONE DERIVATIVE; SODIUM BOROHYDRIDE; TITANIUM DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; COMBINATORIAL LIBRARY; CYCLIZATION; INTERMETHOD COMPARISON; METHODOLOGY; OXIDATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 4944255834     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049939x     Document Type: Article

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35. A general experimental procedure for the RCM and oxidation of DDQ to 16 is as follows: To a stirred solution of 0.05 mM α-amino-acrylic amide 15 in 20 mL of dry, degassed DCM, a second-generation Grubbs catalyst 2 (10 mol %) in 20 mL of dry, degassed DCM was added drop-wise to the mixture under and argon atmosphere at room temperature for ∼12 to 36 h. After removal of most of the solvent in vacuo, 23 mg of DDQ was added to the residue (in ∼5 mL DCM). The mixture was stirred for 2 h at room temperature, and the residue was purified using silica gel chromatography to afford the desired product 16.