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

Muhammad Siddiq Maarop; Fatin Nur Ain Abdul Rashid; Mohd Fazli Mohammat; Zurina Shaameri; Saiful Azmi Johari; Mazurah Mohamed Isa; Anis Low Muhammad Low

doi:10.22146/ijc.39566

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

https://doi.org/10.22146/ijc.39566

Muhammad Siddiq Maarop⁽¹⁾, Fatin Nur Ain Abdul Rashid⁽²⁾, Mohd Fazli Mohammat^(3*), Zurina Shaameri⁽⁴⁾, Saiful Azmi Johari⁽⁵⁾, Mazurah Mohamed Isa⁽⁶⁾, Anis Low Muhammad Low⁽⁷⁾

(1) Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, Malaysia
(2) Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, Malaysia
(3) Organic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(4) Organic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(5) Antimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, Malaysia
(6) Antimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, Malaysia
(7) Atta-ur-Rahman Institute (AURINS), Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(*) Corresponding Author

Abstract

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.

Keywords

four-component reactions; pyrano[2,3-c]pyrazole-3-carboxylate; diethyloxaloacetate

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DOI: https://doi.org/10.22146/ijc.39566