New Efficient Synthesis of 1,4-Benzodiazepin-5-ones by Catalytic Aza-Wittig Reaction

摘要

1,4-Benzodiazepin-5-ones were synthesized in 71-89% yields from 2-isocyanato-/V-(2-oxoalkyl)benzamides via a new catalytic intramolecular aza-Wittig reaction. Starting from easily accessible phthalic anhydride and a-arylamino ketones, the corresponding 2-[[(2-oxoalkyl)amino]carbonyl}benzoic acids underwent sequential formation of the acid azide and Curtis rearrangement to give 2-isocyanato-N-(2-oxoalkyl)benzamides that were reacted directly to give the final 2,4-diaryl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones and 4-aryl-2-tert-bu-tyl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones.