An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones.
We describe herein a convenient approach for the general synthesis of novel tricyclic scaffolds incorporating a fusion of the 1,2,3-triazole ring with difficultly obtainable medium sized rings such as [1,4]benzodiazepin-5-ones and [1,5]benzodiazocin-6-ones through Sonogashira coupling of an aryl iodide with 2-amino-N-methyl-N-(prop-2-ynyl)benzamide or homologue followed by in situ diazotisation, azidation and cycloaddition reactions. The strategy also allows easy accessibility of the corresponding amide-reduced analogues. The operational simplicity and easy substrate availability make the process cost effective and practical.
Chowdhury
Chinmay
C
Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Kolkata, 700032, India. chinmay@iicb.res.in
Sasmal
Anup Kumar
AK
Achari
Basudeb
B
D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry; D001569:Benzodiazepines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D001392:Azocines; D014230:Triazoles; D001569:Benzodiazepines