European Journal of Chemistry 2011, 2(3), 317-323. doi:10.5155/eurjchem.2.3.317-323.420

Reactions with hydrazonoyl halides 65: Synthesis of some new 1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines containing pyrazole moiety


Abdou Osman Abdelhamid (1,*) , Abdelgawad Ali Fahmi (2) , Karema Noury Mahmoud Halim (3)

(1) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(2) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(3) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(*) Corresponding Author

Received: 19 Mar 2011, Accepted: 02 May 2011, Published: 30 Sep 2011

Abstract


2,3-Dihydro-1,3,4-thiadiazoles, and triazolino[4,3-a]pyrimidines containing pyrazole moieties were prepared from the reaction of alkyl 2-[1-(4-cyano-1,5-diphenyl-1H-pyrazol-3-yl)ethylidene]hydrazinecarbodithioate and pyrimidine-2-thione derivatives with appropriate hydrazonoyl halides. The structures of all the newly synthesized compounds were confirmed by elemental analyses, spectral data, and alternative route of synthesis whenever possible.

2_3_317_323_800


Keywords


Pyrazoles; Nitrilimines; 1,3,4-Thiadiazoles; Hydrazonoyl halides; Pyrimidine-2-thione; Triazolino[4,3-a]pyrimidines

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DOI: 10.5155/eurjchem.2.3.317-323.420

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[1]. Assia Sid, Nouara Ziani, Ouafa Demmen-Debbih, Mahieddine Mokhtari, Kaddour Lamara
Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one
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[2]. Abdou Osman Abdelhamid, Abdelgawad Ali Fahmi, Abeer Bahlol Ali
Reactions with hydrazonoyl halides 66: Synthesis of some new 1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines and isoxazolo[3,4-d]pyridazines containing coumarin moiety
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[3]. Abdou Osman Abdelhamid, Nadia Abdelhamid Abdel-Riheem, Tamer Tawhid El-Idreesy, Huda Refat Mahmoud Rashdan
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[4]. M. E. A. Khalifa, M. A. Amin, M. A. N. Mosselhi
Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity
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DOI: 10.1134/S1068162014010075
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[5]. Abdou Osman Abdelhamid, Abdelgawad Ali Fahmi, Amna Ali Mohamed Alsheflo
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References

[1]. Trost, B. M. Chem. Rev. 1978, 78, 363-382.
http://dx.doi.org/10.1021/cr60314a002

[2]. Ganellin, R. J. Med. Chem. 1981, 24, 913-920.
http://dx.doi.org/10.1021/jm00140a001
PMid:6120235

[3]. Dogan, H. N.; Rollas, S.; Erdeniz, H. Farmaco. 1998, 53, 462-467.
http://dx.doi.org/10.1016/S0014-827X(98)00049-4

[4]. Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Uysal, M. K.; Gulen, D. Bioorg. Med. Chem. 2002, 10, 2893-2898.
http://dx.doi.org/10.1016/S0968-0896(02)00143-8

[5]. Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok, G. Farmaco. 2002, 57, 101-107.
http://dx.doi.org/10.1016/S0014-827X(01)01176-4

[6]. Karakus, S.; Rollas, S. Farmaco. 2002, 57, 577-581.
http://dx.doi.org/10.1016/S0014-827X(02)01252-1

[7]. Terzioglu, N.; Gursoy. A. Eur. J. Med. Chem. 2003, 38, 781-786.
http://dx.doi.org/10.1016/S0223-5234(03)00138-7

[8]. Stetter, H.; Rauscher, E. Chem. Ber. 1960, 93, 2054-2057.
http://dx.doi.org/10.1002/cber.19600930922

[9]. Ryan, A. J.; Welling, P. G.; Wright, S. E. Food. Cosmet. Toxicol. 1969, 7(4), 287-295.
http://dx.doi.org/10.1016/S0015-6264(69)80364-0

[10]. Ebnother, A.; Jucker, E.; Lindenmann, A. Helv. Chim. Acta 1959, 42, 1201-1214.
http://dx.doi.org/10.1002/hlca.19590420415

[11]. Burger, A. Medicinal Chemistry, 2nd ed. Interscience, New York, 1945, pp. 345.

[12]. Kueffner, K.; Marx, P.; Laessig, W. Ger. Offen. DE 3, 217, 877 17 Nov 1983, pp. 53. Chem. Abstr., 100, 183105p (1984).

[13]. Abolin, A. G.; Balabanov E. I.; Bespalov, B. P.; Bukin, Y. I.; Rumyantsev, B. M.; Titov, V. V.; Yudina, G. I. Zh. Nauch. Prikl. Fotogr. 1981, 26, 182-193.

[14]. Abdelhamid, A. O.; Abdelall, E. K. A.; Zaki, Y. H. J. Heterocycl. Chem. 2010, 47, 477-482.

[15]. Abdelhamid, A. O.; Afifi, M. A. M. J. Adv. Res. 2010, 1, 137-144.
http://dx.doi.org/10.1016/j.jare.2010.03.005

[16]. Abdelhamid, A. O.; Afifi, M. A. M. Synthetic Commun. 2010, 40, 1539-1550.
http://dx.doi.org/10.1080/00397910903100726

[17]. Abdelhamid, A. O.; Abdelall, E. K. A.; Abdel-Riheem, N. A.; Ahmed, S. A. Phosphorus, Sulfur, Silicon and Relat. Elem. 2010, 185, 709-718.
http://dx.doi.org/10.1080/10426500902922933

[18]. Abdelall, E. K. A.; Mohamed, M. A.; Abdelhamid, A. O. Phosphorus, Sulfur, Silicon and Relat. Elem. 2010, 185, 1862-1874.
http://dx.doi.org/10.1080/10426500903348013

[19]. Abdelhamid, A. O. J. Heterocycl. Chem. 2009, 46, 680-686.
http://dx.doi.org/10.1002/jhet.141

[20]. Abdelhamid, A. O.; Ismail, Z. H.; Abdel-Gawad, S. M.; Ghorab, M. M.; Abdel-Aziem, A. Phosphorus, Sulfur, Silicon and Relat. Elem. 2009, 184, 58-75.
http://dx.doi.org/10.1080/10426500802077630

[21]. Rupe, H. Chem. Ber. 1897, 30, 1097-1100.
http://dx.doi.org/10.1002/cber.189703001211

[22]. Abdallah, M. A. Z. Naturforsch, 2002, 57b, 699-706.

[23]. Abdelhamid, A. O.; Parkanyi, C.; Shawali, A. S.; Abdalla, M. A. J. Heterocycl. Chem. 1984, 21, 1049-1054.
http://dx.doi.org/10.1002/jhet.5570210425

[24]. Emam, H. A.; Abdelhamid, A. O. Phosphorus, Sulfur, Silicon and Relat. Elem. 1997, 131, 37-48.
http://dx.doi.org/10.1080/10426509708031594

[25]. Abdelhamid, A. O.; Emam, H. A.; Abdel-Reheem, N. A. J. Chem. Res. 1999, 532, 2323-2335.

[26]. Abdelhamid, A. O.; Abdelaziz, H. M. Phosphorus, Sulfur, Silicon and Relat. Elem. 2007, 182, 2791-2800.
http://dx.doi.org/10.1080/10426500701521548


How to cite


Abdelhamid, A.; Fahmi, A.; Halim, K. Eur. J. Chem. 2011, 2(3), 317-323. doi:10.5155/eurjchem.2.3.317-323.420
Abdelhamid, A.; Fahmi, A.; Halim, K. Reactions with hydrazonoyl halides 65: Synthesis of some new 1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines containing pyrazole moiety. Eur. J. Chem. 2011, 2(3), 317-323. doi:10.5155/eurjchem.2.3.317-323.420
Abdelhamid, A., Fahmi, A., & Halim, K. (2011). Reactions with hydrazonoyl halides 65: Synthesis of some new 1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines containing pyrazole moiety. European Journal of Chemistry, 2(3), 317-323. doi:10.5155/eurjchem.2.3.317-323.420
Abdelhamid, Abdou, Abdelgawad Ali Fahmi, & Karema Noury Mahmoud Halim. "Reactions with hydrazonoyl halides 65: Synthesis of some new 1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines containing pyrazole moiety." European Journal of Chemistry [Online], 2.3 (2011): 317-323. Web. 16 Sep. 2019
Abdelhamid, Abdou, Fahmi, Abdelgawad, AND Halim, Karema. "Reactions with hydrazonoyl halides 65: Synthesis of some new 1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines containing pyrazole moiety" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.3.317-323.420

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