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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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Funding information
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]. 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
DOI: 10.5155/eurjchem.7.4.468-472.1508
[2]. Yu Zhang, Jing Sun, Guo-Liang Shen, Chao-Guo Yan
Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction
Organic & Biomolecular Chemistry 15(38), 8072, 2017
DOI: 10.1039/C7OB01860F
[3]. 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
DOI: 10.1002/ejoc.201800580
[4]. Afaf Abdel Hameed, Essam Khalaf Ahmed, Asmaa A. Abdel Fattah, Carlos Kleber Z. Andrade, Kamal Usef Sadek
Green and efficient synthesis of polyfunctionally substituted cinnolines under controlled microwave irradiation
Research on Chemical Intermediates 43(10), 5523, 2017
DOI: 10.1007/s11164-017-2944-1
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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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