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Alginic acid: A mild and renewable bifunctional heterogeneous biopolymeric organocatalyst for efficient and facile synthesis of polyhydroquinolines

Author:
Dekamin, Mohammad G., Karimi, Zahra, Latifidoost, Zahra, Ilkhanizadeh, Siamand, Daemi, Hamed, Naimi-Jamal, M. Reza, Barikani, Mehdi
Source:
International journal of biological macromolecules 2018 v.108 pp. 1273-1280
ISSN:
0141-8130
Subject:
Lewis acids, Phaeophyceae, aldehydes, alginates, ammonium acetate, catalytic activity, cost effectiveness
Abstract:
Alginic acid, a widely used naturally occurring carbohydrate which is generally derived from brown seaweeds, can be considered as a bifunctional heterogeneous and green biopolymeric organocatalyst. Alginic acid, without any post-modification with active Bronsted or Lewis acid centers, was found to be a highly active, cost-effective, commercially-available, renewable and recoverable heterogeneous biopolymeric organocatalyst for the expeditious synthesis of polyhydroquinolines (PHQs). Polyhydroquinolines were synthesized from the four-component Hantzsch reaction of ethyl acetoacetate, different aldehydes, ammonium acetate and cyclic 1,3-diones under mild conditions in high to quantitative yields, 75–97%, using alginic acid. Furthermore, alginic acid was found to be reusable for at least 6 consecutive cycles without considerable loss of its catalytic activity.
Agid:
5861905