A New Strategy for the Synthesis of Diverse Benzo[a]carbazoles via Divergent Catalytic Michael Reaction

Kripalaya Ratheesh Arya, Hazel Sparkes, Karnam Jayarampillai Rahendra Prasad

Research output: Contribution to journalArticle (Academic Journal)peer-review

7 Citations (Scopus)
255 Downloads (Pure)

Abstract

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 an unreported imino and amino functionalized spiro[acenaphthylene-8',4-benzo[a]carbazole] hybrids via amine-controlled divergent reactions. The spiro products also were 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 view point of diversity-oriented one-pot synthesis of benzo[a]carbazole derivatives from simple starting materials.
Original languageEnglish
JournalOrganic and Biomolecular Chemistry
Early online date20 Mar 2018
DOIs
Publication statusE-pub ahead of print - 20 Mar 2018

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