Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination
| Autor: | Manisha Mishra, Clifford J. Ellstrom, Béla Török, Roman Dembinski, Dylan J. Twardy, Kraig A. Wheeler |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Ethanol 010405 organic chemistry Imine Aromatization Alkyne Regioselectivity 010402 general chemistry 01 natural sciences Pollution Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Environmental Chemistry Hydroamination Isoquinoline |
| Zdroj: | Green Chemistry. 21:99-108 |
| ISSN: | 1463-9270 1463-9262 |
| DOI: | 10.1039/c8gc02520g |
| Popis: | An efficient environmentally benign route for the synthesis of benzimidazo[2,1-a]isoquinoline has been developed by reacting 2-ethynylbenzaldehyde and related substituted alkynylbenzaldehydes with variously substituted ortho-phenylenediamines and aliphatic amines in ethanol. This method provides a convenient, room temperature, atom-economical, and catalyst-free access to diversely substituted isoquinoline fused benzimidazoles. Regioselectivity of the reaction, as referred to o-phenylenediamines, was confirmed by X-ray crystallography. The reaction was found to occur in three major steps (imine formations, cyclization, and aromatization) and a mechanism has been proposed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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