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- Title
A facile and efficient one-pot procedure for the synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles in PEG-400 and glycerol.
- Authors
Kale, Arun D.; Pawara, Rahul H.; Patel, Harun M.; Dalal, Dipak S.
- Abstract
We have developed a simple and efficient method for synthesizing 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles using catalytic role of recyclable PEG-400 and glycerol at 100 ºC. A total of 15 kojic acid derivatives were synthesized via a one-pot three-component reaction between substituted aromatic aldehydes, malononitrile, and kojic acid with good to excellent yields ranging from 70 to 94% within 0.5–5 h using PEG-400 and 1–6 h using glycerol. The method is characterized by operational simplicity, high yields, and an easy work-up process, as well as being environmentally friendly and avoiding the use of complex catalysts and toxic solvents. Furthermore, the protocol allows for the recycling of PEG-400 and glycerol and can be reused for up to three cycles without appreciable loss in reactivity. We have performed an in-silico study of all the synthesized compounds. Based on the in-silico study, compounds 4ao, 4aa, 4ai, and 4ah showed the better binding affinity towards DNA gyrase protein and these four compounds demonstrates their potential as drug-like molecules by complying with Lipinski's rule and Jorgensen's rule, and all their pharmacokinetic parameters were within the acceptable range.
- Subjects
AROMATIC aldehydes; GLYCERIN; DNA topoisomerase II; ACID derivatives; CHEMICAL synthesis; MALONONITRILE
- Publication
Research on Chemical Intermediates, 2024, Vol 50, Issue 2, p853
- ISSN
0922-6168
- Publication type
Article
- DOI
10.1007/s11164-023-05188-z