Synthesis of benzo[ a ]carbazole derivatives via intramolecular cyclization using Brønsted acidic carbonaceous material as the catalyst

In this work, a new procedure for the synthesis of benzo[ a ]carbazole from 1,3-diketones, primary amines, phenylglyoxal monohydrate, and malononitrile employing a solid acidic catalyst has been developed. The multicomponent reaction provided 3-cyanoacetamide pyrrole as an intermediate and then the...

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Bibliographic Details
Published in:RSC advances 2023-09, Vol.13 (41), p.28623-28631
Main Authors: Nguyen, Hai Truong, Nguyen, Phat Ngoc, Van Le, Tan, Nguyen, Trinh Hao, Nguyen, Linh Dieu, Tran, Phuong Hoang
Format: Article
Language:English
Subjects:
Amines
Carbazoles
Carbonaceous materials
Catalysts
Chemistry
Diketones
Malononitrile
Sulfonic acid
Synthesis
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Summary:In this work, a new procedure for the synthesis of benzo[ a ]carbazole from 1,3-diketones, primary amines, phenylglyoxal monohydrate, and malononitrile employing a solid acidic catalyst has been developed. The multicomponent reaction provided 3-cyanoacetamide pyrrole as an intermediate and then the formation of benzo[ a ]carbazole via intramolecular ring closure. The reaction was carried out for 2 h at 240 °C, resulting in the desired product with 73% yield. Acidic sites on the solid acid catalyst, made from rice husk-derived amorphous carbon with a sulfonic acid core (AC-SO 3 H), provided the best activity. Acidic sites on the surface of the catalyst, including carboxylic, phenolic, and sulfonic acids, were 4.606 mmol g −1 of the total acidity. AC-SO 3 H demonstrated low cost, low toxicity, porosity, stability, and flexibility of tuning and reusability.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra04943d