New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity
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 in...
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doaj-b430d1dd268648cc8e7db32b9b1ad9a42020-11-25T01:40:31ZengUniversitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782019-12-01201607110.22146/ijc.3956624101New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial ActivityMuhammad Siddiq Maarop0Fatin Nur Ain Abdul Rashid1Mohd Fazli Mohammat2Zurina Shaameri3Saiful Azmi Johari4Mazurah Mohamed Isa5Anis Low Muhammad Low6Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, MalaysiaDepartment of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, MalaysiaOrganic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, MalaysiaOrganic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, MalaysiaAntimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, MalaysiaAntimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, MalaysiaAtta-ur-Rahman Institute (AURINS), Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, MalaysiaA 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.https://jurnal.ugm.ac.id/ijc/article/view/39566four-component reactionspyrano[2,3-c]pyrazole-3-carboxylatediethyloxaloacetate |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Muhammad Siddiq Maarop Fatin Nur Ain Abdul Rashid Mohd Fazli Mohammat Zurina Shaameri Saiful Azmi Johari Mazurah Mohamed Isa Anis Low Muhammad Low |
spellingShingle |
Muhammad Siddiq Maarop Fatin Nur Ain Abdul Rashid Mohd Fazli Mohammat Zurina Shaameri Saiful Azmi Johari Mazurah Mohamed Isa Anis Low Muhammad Low New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity Indonesian Journal of Chemistry four-component reactions pyrano[2,3-c]pyrazole-3-carboxylate diethyloxaloacetate |
author_facet |
Muhammad Siddiq Maarop Fatin Nur Ain Abdul Rashid Mohd Fazli Mohammat Zurina Shaameri Saiful Azmi Johari Mazurah Mohamed Isa Anis Low Muhammad Low |
author_sort |
Muhammad Siddiq Maarop |
title |
New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity |
title_short |
New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity |
title_full |
New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity |
title_fullStr |
New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity |
title_full_unstemmed |
New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity |
title_sort |
new access to pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via domino four-component reaction and their antimicrobial activity |
publisher |
Universitas Gadjah Mada |
series |
Indonesian Journal of Chemistry |
issn |
1411-9420 2460-1578 |
publishDate |
2019-12-01 |
description |
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. |
topic |
four-component reactions pyrano[2,3-c]pyrazole-3-carboxylate diethyloxaloacetate |
url |
https://jurnal.ugm.ac.id/ijc/article/view/39566 |
work_keys_str_mv |
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