A concise route to triazolobenzodiazepine derivatives via a one-pot alkyne-azide cycloaddition reaction.
A new and efficient one-pot synthesis of [1,2,3]triazolo[1,5-a][1,4] benzodiazepin-6(4H)-ones is described starting from readily available anthranilic acids. A small array of the title compounds were assembled via a four-step sequence involving diazotisation, azide addition followed by amide bond formation employing polymer supported carbodiimide and subsequent 1,3-dipolar cycloaddition reaction.
Thomas
Andrew W
AW
F. Hoffmann-La Roche AG, Pharmaceuticals Division, Discovery Chemistry, Basel, CH 4070, Switzerland. andrew.thomas@roche.com
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002234:Carbodiimides / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D011108:Polymers / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*; D062367:ortho-Aminobenzoates / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D002234:Carbodiimides; D002712:Chlorides; D011108:Polymers; D014230:Triazoles; D062367:ortho-Aminobenzoates; D001569:Benzodiazepines