Synthesis of novel annelated systems based on the interaction and reactivity estimation of amino‐1,5‐benzodiazepin‐2‐ones with dimethyl‐2‐oxoglutaconate

Abstract

Abstract magnified image A number of substituted tetracyclic 4H‐[1,4]diazepino[3,2,1‐hi]pyrido[4,3,2‐cd]indole and tricyclic 1H‐[1,4]diazepino[2,3‐g] or [2,3‐h]quinoline derivatives were prepared from 7‐ (or 8, or 9)amino‐1,5‐benzodiazepin‐2‐ones by the Doebner–von Miller quinoline synthesis. The structure of the cyclized products depends on the position of the primary amino group and on the substituents of the diazepine ring of the starting compounds. The regiochemical outcome of the reaction was estimated by calculating average local ionization energies on the molecular surface at the Density Functional Theory (DFT) level of theory. J. Heterocyclic Chem., (2009).