A new strategy for the synthesis of diverse benzo[a]carbazoles via a divergent catalytic Michael reaction
| Autor: | Karnam Jayarampillai Rajendra Prasad, Arya Kripalaya Ratheesh, Hazel A. Sparkes |
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| Rok vydání: | 2018 |
| Předmět: |
Tandem
010405 organic chemistry Carbazole Stereochemistry Organic Chemistry Carbon-13 NMR 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Amino functionalized Catalysis chemistry.chemical_compound chemistry Michael reaction Physical and Theoretical Chemistry Spectral data Malononitrile |
| Zdroj: | Arya, K R, Sparkes, H & Prasad, K J R 2018, ' A New Strategy for the Synthesis of Diverse Benzo[a]carbazoles via Divergent Catalytic Michael Reaction ', Organic and Biomolecular Chemistry . https://doi.org/10.1039/C8OB00154E |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c8ob00154e |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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