Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines

Tetrahedron Letters

Volumn 51, Issue 34, 2010, Pages 4566-4569

  Xu, Zhigang ^a   Dietrich, Justin ^a   Shaw, Arthur Y ^a   Hulme, Christopher ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 TERT BUTYL CYCLOHEXEN 1 YL ISOCYANIDE; BENZODIAZEPINE DERIVATIVE; CYANIDE; QUINOXALINE DERIVATIVE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; REACTION OPTIMIZATION;

EID: 77955710385     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.116     Document Type: Article

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31. For the preparation of 12 and general library protocol: A solution of N-BOC-1,2-phenylenediamine (0.21 g, 1.00 mmol) and ethyl glyoxalate (50%, 0.20 ml, 1.00 mmol) in DCM (1.00 ml) was reacted in microwave at 130°C for 15 min. After the reaction mixture was cooled down to room temperature, appropriate benzoic acid (1.00 mmol), trifluoroethanol (1.0 ml), and 4-tert-butyl cyclohexen-1-yl isocyanide (0.16 g, 1.00 mmol) were added. The resulting solution was stirred overnight, and the solvent was removed in vacuo. The product was purified by column chromatography (hexanes/ethyl acetate, 1:4) to afford a white solid 12 (320 mg, 0.46 mmol).
32. 13C NMR (75 MHz, DMSO) 168.27, 166.12, 137.26, 133.58, 132.30, 130.14, 127.34, 125.15, 121.71, 121.62, 100.67, 79.37, 45.81.