Synthesis of polycyclic 3,3 ' -spirooxindoles and some new 2-arylquinoxalines from ( E/Z )-1-(2-oxo-2-arylethylidene)-5,6-dihydro-4 H -pyrrolo[3,2,1-ij ]quinolin-2(1 H )-ones

A facile protocol to access a novel series of spirocyclodiazepines from cyclocondensation of 1-(2oxo-2-arylethylidene)-5,6-dihydro-4 H -pyrrolo[3,2,1- ij ]quinolin-2(1 H )-ones (derived from 5,6-dihydro-1 H pyrrolo[3,2,1- ij ]quinolone-1,2(4 H )-dione) with ethane-1,2-diamines and benzene-1,2-diamines, generates polycyclic spirooxindoles and unexpectedly produces 2-arylquinoxalines instead of spiro[ indole -1,5benzodiazepines ], respectively, in the presence of p -TSA as an efficient catalyst in a green solvent.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A facile protocol has been developed to synthesize a novel series of polycyclic spirooxindoles and 2-arylquinoxalines from specific compounds.