Zaharani, Lia and Khaligh, Nader Ghaffari and Mihankhah, Taraneh and Johan, Mohd Rafie and Hamizi, Nor Aliya (2020) Facile and green synthesis of a series of dihydro-[1,2,4]triazolo[1,5-a]pyrimidine scaffolds. Canadian Journal of Chemistry-Revue Canadienne De Chimie, 98 (10). pp. 630-634. ISSN 0008-4042, DOI https://doi.org/10.1139/cjc-2020-0145.
Full text not available from this repository.Abstract
This work presents a new catalytic application of 4,4'-trimethylenedipiperidine for the efficient synthesis of a series of dihydro-[1,2,4] triazolo[1,5-a]pyrimidines. According to the principles of green chemistry, the reaction was performed (a) in a solvent mixture comprised of water and ethanol (1:1 v/v) at reflux temperature and (b) solvent-free grinding in a mortar by a pestle. The organocatalyst could be reused up to 10 runs, and no reduction of catalytic activity was detected. A variety of substituted dihydro-[1,2,4] triazolo[1,5-a]pyrimidines were obtained in good to excellent yields under eco-friendly conditions. 4,4'-Trimethylenedipiperidine is commercially available and easy to handle, and it also shows high thermal stability and good solubility in water. This work revealed that this organocatalyst, a hydrogen bond donor to active carbonyl groups and simultaneously a Lewis base through the nitrogen atom of second piperidine moiety, could play a vital role in the promotion of the one-pot multi-component reactions. The main merits of the current methodology include short reaction time, wide substrate scope, use of a metal-free catalyst and green solvents, and simple work-up process. Furthermore, this organocatalyst can be an alternative to piperidine for organic transformations. © 2020, Canadian Science Publishing. All rights reserved.
| Item Type: | Article |
|---|---|
| Funders: | High Impact Research Grant (NANOCAT RU001-2019) for Scientific Research from the University of Malaya, Malaysia |
| Uncontrolled Keywords: | Annulation; Heterocycles; One-pot synthesis; Organocatalyst; Three-component reaction |
| Subjects: | T Technology > TA Engineering (General). Civil engineering (General) |
| Divisions: | Deputy Vice Chancellor (Research & Innovation) Office > Nanotechnology & Catalysis Research Centre |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 08 Feb 2021 08:40 |
| Last Modified: | 08 Feb 2021 08:40 |
| URI: | http://eprints.um.edu.my/id/eprint/25729 |
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