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New three-component domino reactions, providing divergent approaches to multifunctionalized pyrroles with different substitution patterns, have been established (47 examples). In this work, a new rearrangement of quinoxalinones with the participation of the in situ-generated 2-en-1-imine moiety of the substituent at C3 makes it possible to construct two new heterocyclic systems, namely, a benzimidazolone and a pyrrole, simultaneously under one-pot reaction conditions. The reaction is easy to perform simply by mixing three common reactants of acetic acid with heating. Secondary amines or primary alcohols as the third component of the reaction, along with quinoxalin-3­(4H)-ones and malononitrile, not only initiate the rearrangement but also are responsible for the nature of substituents at position 5 of the pyrrole ring in the newly formed new biheterocyclic system. The reaction proceeds smoothly and can be finished within 7 h, which makes workup convenient to give up to 97% chemical yields.

A new process has been developed for the bromine-promoted sequential (sp2)C = (sp2)C bond functionalization of (E)-3-styrylquinoxalin-2­(1H)-ones and furo­[b]­annulation via the 5-exo-cyclization in dimethyl sulfoxide (DMSO). The reaction represents a novel strategy for the synthesis of 2-aryl-3-(methylthio)­furo­[2,3-b]­quinoxalines and involves 3-(1,2-dibromo-2-arylethyl)­quinoxalin-2­(1H)-ones and 2-arylfuro­[2,3-b]­quinoxalines as key intermediates. Furthermore, DMSO was converted to dimethyl sulfide in situ, which served as the methylthiolation reagent in the reaction. This protocol constitutes an efficient and convenient method for the annulation and methylthiolation of (E)-3-styrylquinoxalin-2­(1H)-ones bearing a wide range of functional groups in high yields at room temperature.

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