A new strategy for the synthesis of diverse benzo[ a] carbazoles via a divergent catalytic Michael reaction

作者：Ratheesh Arya Kripalaya; Sparkes Hazel A; Prasad Karnam Jayarampillai Rajendra^*

来源：Organic and Biomolecular Chemistry, 2018, 16(14): 2527-2540.

DOI：10.1039/c8ob00154e

A new type of divergent tandem Michael addition of ,-dicyanomethylidenecarbazoles with -nitrostyrenes afforded multifunctional benzo[a]carbazoles [BCs] and benzodihydro[a]carbazoles [BDHCs] in good yields. In addition, the direct multicomponent transformation of ,-dicyanomethylidenecarbazoles, acenaphthenequinone and malononitrile results in the formation of unreported imino and amino functionalized spiro[acenaphthylene-8,4-benzo[a]carbazole] hybrids via amine-controlled divergent reactions. The spiro products were also obtained in good yields. The structures of the synthesized cycloadducts were confirmed by elemental analysis, spectral data (FT-IR, H-1, C-13 NMR and HRMS) and by single-crystal X-ray diffraction studies.The application of this divergent tandem Michael addition protocol is beneficial from the viewpoint of the diversity-oriented one-pot synthesis of benzo[a]carbazole derivatives from simple starting materials.

• 出版日期2018-4-14