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Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines
Douaa Salman AlMarzouq (1,*)
, Omniya Sayed Zaky (2) , Abdulaziz Abdulrazaq AlNajjar (3) , Kamal Usef Sadek (4) (1) Department of Chemistry, Faculty of Science, South Valley University, Qena, 83511, Egypt
(2) Department of Chemistry, Faculty of Science, South Valley University, Qena, 83511, Egypt
(3) Department of Applied Science, Faculty of Technological Studies, Public Authority for Applied Education and Training, 42325 Safat, 70654, Kuwait
(4) Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt
(*) Corresponding Author
Received: 30 Jun 2016 | Revised: 05 Jul 2016 | Accepted: 23 Jul 2016 | Published: 30 Sep 2016 | Issue Date: September 2016
Abstract
Pyrazole molecules are in the forefront of organic chemistry due to their various encompass substituents, which have many biological activity sequence. The biological and medicinal activities of pyrazolo[1,5-a]pyrimidines have received considerable interest in this regard. We reported here a comparison between reaction of 4-phenylazo-3,5-diaminopyrazole (4) with ethyl propiolate (15), dimethylacetylene dicarboxylate (20), diethyl fumarate (25) and benzylidenemalononitrile (11) in the presence of catalytic amount of piperidine. We initially followed literature procedure (method A), then utilizing ultrasound irradiation (method B), microwave heating (method C) and in a Q-tube (method D). We confirmed the structure of the product by analytical spectroscopic methods. Method (D) gave a good yield with a record reaction time.
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DOI: 10.5155/eurjchem.7.3.347-351.1473
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Kuwait University, Analytical Analab/SAF facilities provided by General Facility-Science (GF-S) (Project No: GS 01/01, GS 01/03, GS 01/05, GS 02/10 & GS 03/08), Kuwait.
Citations
[1]. AbdElAziz A. Nayl, Hamada Mohamed Ibrahim, Kamal M. Dawood, Wael A. A. Arafa, Ahmed I. Abd-Elhamid, Ismail M. Ahmed, Mohamed A. Abdelgawad, Hazim M. Ali, Ibrahim Hotan Alsohaimi, Ashraf A. Aly, Stefan Bräse, Asmaa Kamal Mourad
High-Pressure Metal-Free Catalyzed One-Pot Two-Component Synthetic Approach for New 5-Arylazopyrazolo[3,4-b]Pyridine Derivatives
Molecules 27(19), 6369, 2022
DOI: 10.3390/molecules27196369
[2]. Douaa Salman AlMarzouq
Reactions under increased pressure: The reactivity of functionally substituted 3-oxo-2-arylhydrazones toward active methylene reagents in Q-tube
European Journal of Chemistry 12(2), 154, 2021
DOI: 10.5155/eurjchem.12.2.154-158.2065
[3]. Kamal Usef Sadek, Maghraby Ali Selim, Abdul-Aziz Alnajjar, Mohamed Atallah, Mohamed Hilmy Elnagdi
Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube
European Journal of Chemistry 7(4), 468, 2016
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[4]. Yu Zhang, Jing Sun, Guo-Liang Shen, Chao-Guo Yan
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Organic & Biomolecular Chemistry 15(38), 8072, 2017
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[5]. Felipe S. Stefanello, Yuri G. Kappenberg, Juliane N. Araújo, Steffany Z. Franceschini, Marcos A.P. Martins, Nilo Zanatta, Bernardo A. Iglesias, Helio G. Bonacorso
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Applied Organometallic Chemistry 36(10), , 2022
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[7]. Mohammed Loubidi, Catherine Manga, Zahira Tber, Ibtissam Bassoude, El Mokhtar Essassi, Sabine Berteina-Raboin
One-Pot SN Ar/Direct Pd-Catalyzed CH Arylation Functionalization of Pyrazolo[1,5-a ]pyrimidine at the C3 and C7 Positions
European Journal of Organic Chemistry 2018(29), 3936, 2018
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DOI Link: https://doi.org/10.5155/eurjchem.7.3.347-351.1473
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European Journal of Chemistry 2016, 7(3), 347-351 | doi: https://doi.org/10.5155/eurjchem.7.3.347-351.1473 | Get rights and content
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