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

文献情報

出版日 2018-03-20

DOI 10.1039/C8OB00154E

インパクトファクター 3.876

著者

Arya Kripalaya Ratheesh, Hazel A. Sparkes, Karnam Jayarampillai Rajendra Prasad

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要旨

A new type of divergent tandem Michael addition of α,α-dicyanomethylidenecarbazoles with β-nitrostyrenes afforded multifunctional benzo[a]carbazoles [BCs] and benzodihydro[a]carbazoles [BDHCs] in good yields. In addition, the direct multicomponent transformation of α,α-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, 1H, 13C 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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

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