New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity

• Main Authors: Muhammad Siddiq Maarop, Fatin Nur Ain Abdul Rashid, Mohd Fazli Mohammat, Zurina Shaameri, Saiful Azmi Johari, Mazurah Mohamed Isa, Anis Low Muhammad Low
• Format: Article
• Language: English
• Published: Universitas Gadjah Mada 2019-12-01
• Series: Indonesian Journal of Chemistry
• Subjects: four-component reactions; pyrano[2,3-c]pyrazole-3-carboxylate; diethyloxaloacetate
• Online Access: https://jurnal.ugm.ac.id/ijc/article/view/39566
• ISSN: 1411-9420; 2460-1578

A library of some novel classes of pyrano[2,3-c]pyrazole-3-carboxylates was synthesized by employing uncatalyzed domino four-component reaction using diethyloxaloacetate, hydrazine hydrate, aldehydes and malononitrile in refluxing of ethanol-acetic acid solvent systems. Series of domino reactions involving of pyrazolone formation, Michael addition, and Thorpe-Ziegler cyclization reaction managed to produce the cyclized products from moderate to excellent yield. This protocol provides a reliable, general and salient procedure for the title compound using a one-pot approach. Preliminary biological screening unveiled limited potentials of this class of compounds for antimicrobial lead compound due to its limited solubility properties.