A mild, one-pot preparation of 1,3,4-oxadiazoles

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6435-6439

  Li, Changkun ^a   Dickson, Hamilton D ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; ALKENE; ALKYNE; CARBAMIC ACID; CARBOXYLIC ACID; ESTER; HALIDE; HYDRAZIDE; NITRILE; PHENOL; REAGENT; SULFONAMIDE;

ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ONE POT SYNTHESIS; REACTION OPTIMIZATION; REACTION TIME; ROOM TEMPERATURE; STEREOSPECIFICITY;

EID: 77955853232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.084     Document Type: Article

References (19)

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19. Typical experimental procedure:(Table 2, entry 4) 2-(3-buten-1-yl)-5- phenyl-1,3,4-oxadiazole: A solution of benzohydrazide (150 mg, 1.102 mmol),4-pentenoic acid (110 mg, 1.102 mmol), HATU (419 mg, 1.102 mmol), and Hunig's base (0.385 mL, 2.203 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 45 min. Next, Burgess reagent (656 mg, 2.75 mmol) was added and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was adsorbed onto silica gel and the crude material was purified via silica gel chromatography (5-40% ethyl acetate/hexanes as eluent) to give 2-(3-buten-1-yl)-5-phenyl-1,3,4-oxadiazole (194 mg, 88% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (dd, J = 7.78, 1.74 Hz, 2 H), 7.54-7.62 (m, 3H), 5.88 (m, 1H), 5.10 (dd, J = 17.03, 1.65 Hz, 1H), 5.01 (dd, J =10.26, 1.47 Hz, 1h), 3.03 (t, J = 7.42 Hz, 2h), 2.51-2.55 (m, 2H). LC-MS (ES+) m/z, 200.63 [M+H].