European Journal of Chemistry 2016, 7(3), 347-351. doi:10.5155/eurjchem.7.3.347-351.1473

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, Accepted: 23 Jul 2016, Published: 30 Sep 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.


Keywords


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

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DOI: 10.5155/eurjchem.7.3.347-351.1473

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Citations

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[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
/

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. 21 Sep. 2019
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)

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

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