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Synthesis of new triazolo[1,5-b][2,4]benzodiazepines via tandem cyclization of o-(azidomethyl)benzoates with cyanoacetamides

Monatsh. Chem. 2017, 148 (6), 1035-1041

DOI: 10.1007/s00706-016-1905-5

Yakovenko G.; Yagodkina M.; Bol’but A.; Shishkina S.; Vovk M. V.

Based on the tandem anionic cyclization of o-(azidomethyl)benzoates with 2-cyanoacetamides, an efficient synthetic route to the hitherto unknown heterocyclic system, triazolo[1,5-b][2,4]benzodiazepine, has been developed. The optimum reaction conditions have been found which provide 59–74% yields of target compounds. Their structural determination has been performed by the IR, LCMS, and NMR spectral methods as well as by X-ray diffraction analysis.

Synthesis of new triazolo[1,5-b][2,4]benzodiazepines via tandem cyclization of o-(azidomethyl)benzoates with cyanoacetamides

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