Use of Piperidine and Pyrrolidine in Knoevenagel Condensation

Rodrigo De Oliveira Vieira, Edson Nascimento Dos Santos, Gabriela Consolini and Mauri Sergio Alves Palma
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Mauri Sergio Alves Palma: Department of Pharmaceutical and Biochemical Technology, University of São Paulo, Brazil

Organic & Medicinal Chemistry International Journal, 2018, vol. 5, issue 4, 113-116

Abstract: Glitazones are an important class of drugs used specially in the treatment of diabetes mellitus type II. Pharmaceuticals intermediates which originates glitazones can be formed by the reaction of a carbonyl with an activated methylene, though Knoevenagel condesantion using a weak base as catalyst. In this study, tiazolidine-2,4-dione (TZD) was reacted with p-metoxybenzaldehyde and p-nitrobenzaldehyde, using piperidine and pyrrolidine as catalysts. The influence of the substituent was evident, 4-metoxybenzaldehyde showed the highest value of TZD conversion. Pyrrolidine showed higher value of TZD conversion than piperidine for both aldehydes, reaching a conversion of 100% to 4-methoxybenzaldehyde with lower amount of pyrrolidine corresponding to 62.5% of piperidine.

Keywords: juniper publishers:Medicinal Chemistry; Biochemistry Journal; Pharmacology Journal; biochemical pharmacology; molecular pharmacology; biochemistry; open access journals; peer reviewed journals; Open Access; Journal of Molecular Biochemistry; International Research Journal of Pure and Applied Chemistry; World Journal of Biological Chemistry; Biochemistry and Analytical Biochemistry; Biochemistry & Physiology: Open Access; Molecular Biology International; Plant Biochemistry & Physiology; International Journal of Molecular Sciences; Journal of Clinical and Medical Genomics; Environmental Analytical Chemistry; Medicinal Chemistry; Juniper publishers reivews (search for similar items in EconPapers)
Date: 2018
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Persistent link: https://EconPapers.repec.org/RePEc:adp:jomcij:v:5:y:2018:i:4:p:113-116

DOI: 10.19080/OMCIJ.2018.05.555668

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