Micelle-mediated synthesis of quinoxaline, 1,4-benzoxazine and 1,4-benzothiazine scaffolds from styrenes

A range of heterocycles based on quinoxalines, 1,4-benzoxazines and 1,4-benzothiazines have been accessed from styrenes by reacting them with benzene-1,2-diamine, 2-aminophenol and 2-aminothiophenol respectively in micellar medium. This reaction occurring in a less explored cetylpyridinium bromide (CPB) micellar medium operates in the presence of NBS through a tandem hydrobromination-oxidation cascade, converting styrenes to phenacyl bromides. Its subsequent nucleophilic addition with aromatic 1,2-dinucleophiles and further transformations led to the formation of heterocyclic constructs. The locus of the reaction site was confirmed through NMR studies and the types of interactions between the CPB and solubilizates were established by DFT calculations. The formation of quinoxalines, 2-aryl-1,4-benzoxazines and 2-aryl-1,4-thiazines by reacting 1,2-diaminobenzenes and 1,2-aminophenols/thiophenols with styrenes in CPB-micellar medium is reported.