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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Q-tube; High yields; Record time; Green technology; Pyrazolo[1,5-a]pyrimidines; Reactions under increased pressure

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.7.3.347-351.1473

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1517 times | icon graph PDF Article downloaded 642 times

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]. 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
DOI: 10.5155/eurjchem.7.4.468-472.1508
/


[4]. 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
/


[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
Trifluoromethyl-substituted aryldiazenyl-pyrazolo[1,5-a]pyrimidin-2-amines: Regioselective synthesis, structure, and optical properties
Journal of Fluorine Chemistry  255-256, 109967, 2022
DOI: 10.1016/j.jfluchem.2022.109967
/


[6]. Hemmat A. Elbadawy, Bashir A. Abd‐El‐Nabey, Ali El‐Dissouky Ali, Eman Hassan Elsayed
The development of an unexpected Cu(I)‐pyrazolo pyrimidine‐based complex: Synthesis, spectroscopic characterizations, and biological activity
Applied Organometallic Chemistry  36(10), , 2022
DOI: 10.1002/aoc.6843
/


[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
DOI: 10.1002/ejoc.201800580
/


[8]. 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
/


References


[1]. Elnagdi, M. H.; Abd Allah, S. O. J. Prakt. Chem. 1973, 315, 1009-1016.
http://dx.doi.org/10.1002/prac.19733150604

[2]. Braun, H. J. Ger. Offen. 1998, DE 1996143059.

[3]. Sener, N.; Sener, I.; Yavuz, S.; Karci, F. Asian J. Chem. 2015, 27(8), 3003-3012.
http://dx.doi.org/10.14233/ajchem.2015.18769

[4]. Jonas, C.; Karthik, K.; Aleksandras, S.; Asta, J.; Deividas, V.; Algirdas, K.; Mindaugas, V. Cancers 2014, 6(4), 2224-2242.
http://dx.doi.org/10.3390/cancers6042224

[5]. Elkholy, A.; Al-Qalaf, F.; Elnagdi, M. H. Arkivoc 2008, 14, 124-131.

[6]. Elnagdi, M. H.; Kandeel, E. M.; Elmoghayar, M. R. H. Z. Natureforsch. B 1977, 32, 307-310.

[7]. Anwar, H. F.; Fleita, D. H.; Kolshorn, H.; Meier H.; Elnagdi, M. H. Arkivoc 2006, 15, 133-141.

[8]. Behbehani, H.; Ibrahim H. M.; Makhseed, S. Arkivoc 2010, 2, 267-282.

[9]. Abbas-Temerik, H. H.; Abo-Bakr, A. M. Eur. J. Chem. 2016, 7(1), 107-114.
http://dx.doi.org/10.5155/eurjchem.7.1.107-114.1369

[10]. Vaquero, J. J.; Fuentes, L.; Castillo, J. C. D.; Perez, M. I.; Garcia, J. L.; Soto, J. L. Synthesis 1987, 1, 33-35.
http://dx.doi.org/10.1055/s-1987-27831

[11]. Ried, W.; Aboul-Fetouh, S. Tetrahedron 1988, 44(23), 7155-7162.
http://dx.doi.org/10.1016/S0040-4020(01)86083-X

[12]. Konda, S.G. Eur.J. Chem. 2014, 5(4), 676-680.
http://dx.doi.org/10.5155/eurjchem.5.4.676-680.1110

[13]. Chen-Tsai, P.; Wang, I. Dyes Pigments 2005, 64(3), 259-264.
http://dx.doi.org/10.1016/j.dyepig.2004.05.013

[14]. Elnagdi, M. H. Tetrahedron 1974, 30(16), 2791-2796.
http://dx.doi.org/10.1016/S0040-4020(01)97447-2

[15]. Karci, F.; Demircali, A. Dyes Pigments 2007, 74(2), 288-297.
http://dx.doi.org/10.1016/j.dyepig.2006.02.007

[16]. Tsai, P.; Wang, I. Dyes Pigments 2007, 74(3), 578-584.
http://dx.doi.org/10.1016/j.dyepig.2006.03.022

[17]. Al-Sehemi, A. G.; Irfan, A.; Fouda, A. M. Spectrochim. Acta A 2013, 111, 223-229.
http://dx.doi.org/10.1016/j.saa.2013.04.010


How to cite


AlMarzouq, D.; Zaky, O.; AlNajjar, A.; Sadek, K. Eur. J. Chem. 2016, 7(3), 347-351. doi:10.5155/eurjchem.7.3.347-351.1473
AlMarzouq, D.; Zaky, O.; AlNajjar, A.; Sadek, K. Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines. Eur. J. Chem. 2016, 7(3), 347-351. doi:10.5155/eurjchem.7.3.347-351.1473
AlMarzouq, D., Zaky, O., AlNajjar, A., & Sadek, K. (2016). Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines. European Journal of Chemistry, 7(3), 347-351. doi:10.5155/eurjchem.7.3.347-351.1473
AlMarzouq, Douaa, Omniya Sayed Zaky, Abdulaziz Abdulrazaq AlNajjar, & Kamal Usef Sadek. "Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines." European Journal of Chemistry [Online], 7.3 (2016): 347-351. Web. 3 Jun. 2023
AlMarzouq, Douaa, Zaky, Omniya, AlNajjar, Abdulaziz, AND Sadek, Kamal. "Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines" European Journal of Chemistry [Online], Volume 7 Number 3 (30 September 2016)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.7.3.347-351.1473


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.