Abstract
The reaction of thioxopyrimidine derivative 1a with chloroacetic acid and p-chlorobenzaldehyde gave compound 2. Alkylation of 1b using chloroacetonitrile gave N-alkylated derivative 6 which was reacted with hydrazine hydrate to give 7. Compound 7 was cyclized with formic and nitrous acid to give 8 and 9, respectively. The reaction of 1b with phosphorous oxychloride gave chloropyrimidine derivative 10 which was reacted and cyclized with different reagents to give compounds 11–23. The antimicrobial activity was studied against examples of Gram-positive and Gram-negative bacteria.
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References
E. Abdelghani, Conjugate addition reactions of some methylidene 1-benzylpyrimidinetrione derivatives. Heterocycles 55, 2413–2421 (2001)
E. Abdelghani, M.H. Sherif, M.G. Assy, GhM Morsi, Synthesis and reactions of some new pyrimidine thiones. J. Am. Sci. 6, 10–15 (2010)
N.M. Abd El-Salam, N.S. Mostafa, G.A. Ahmed, O.Y. Alothman, Synthesis of pyrimidines and fused pyrimidines and their evaluation of antimicrobial activity. Wulfenia 20, 303–313 (2013)
A.E. Amr, A.M. Mohamed, S.F. Mohamed, N.A. Abdel-Hafez, A.G. Hammam, Anticancer activities of some newly synthesized pyridine, pyrane and pyrimidine derivatives. Bioorg. Med. Chem. 14, 5481–5488 (2006)
M.A. Badawy, S.A.L. Abdel-Hady, Y.A. Ibrahim, A.M. Kadry, Chemistry of quinazolines: reinvestigation of the action of hydrazine on thioxo derivatives. J. Heterocyclic Chem. 22, 1535–1536 (1985)
A. Bazgir, M.M. Khanaposhtani, R. Ghahremanzadeh, A.A. Soorki, A clean, three-component and one-pot cyclo-condensation to pyrimidine-fused heterocyles. C. R. Chim. 12, 1287–1295 (2009)
A.A. Bekhit, H.T.Y. Fahmy, S.A.F. Rostom, A.M. Baraka, Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d] pyrimidines as anti-inflammatory-antimicrobial agents. Eur. J. Med. Chem. 38, 27–36 (2003)
B. Bonev, J. Hooper, J. Parisot, Principles of assessing bacterial susceptibility to antibiotics using the agar diffusion method. J. Antimic. Chemother. 61, 1295–1301 (2008)
M.T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5-carbonitrile derivatives. Bioorg. Med. Chem. 14, 366–372 (2006)
V.S. Dinakaran, K.K. Srinivasan, Synthesis and screening of angularly fused pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-4(3H)-ones. Der Pharma Chemica 3, 62–69 (2011)
Y. Ding, J. Girardet, K.L. Smith, G. Larson, B. Prigaro, J.Z. Wu, N. Yao, Parallel synthesis of 5-cyano-6-aryl-2-thiouracil derivatives as inhibitors for hepatitis C viral NS5B RNA-dependent RNA polymerase. Bioorg. Chem. 34, 26–38 (2006)
E. Dreassi, A.T. Zizzari, M. Mori, I. Filippi, A. Belfiore, A. Naldini, F. Carraro, A. Santucci, S. Schenone, M. Botta, 2-Hydroxypropyl-β-cyclodextrin strongly improves water solubility and anti-proliferative activity of pyrazolo[3,4-d]pyrimidines Src-Abl dual inhibitors. Eur. J. Med. Chem. 45, 5958–5964 (2010)
O.A. Fathalla, S.M. Awad, M.S. Mohamed, Synthesis of new 2-thiouracil-5-sulphonamide derivatives with antibacterial and antifungal activity. Arch. Pharm. Res. 28, 1205–1212 (2005)
O.A. Fathalla, W.A. Zaghary, H.H. Radwan, S.M. Awad, M.S. Mohamed, Synthesis of new 2-thiouracil-5-sulphonamide derivatives with biological activity. Arch. Pharm. Res. 25, 258–269 (2002)
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, N.S. Shetty, Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg. Med. Chem. 14, 2040–2047 (2006)
O.D. Kinzel, R.G. Ball, M. Donghi, C.K. Maguire, E. Muraglia, S. Pesci, M. Rowley, V. Summa, 3-Hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylates—fast access to a heterocyclic scaffold for HIV-1 integrase inhibitors. Tetrahedron Lett. 49, 6556–6558 (2008)
C. Mugnaini, F. Manetti, J.A. Esté, I. Clotet-Codina, G. Maga, R. Cancio, M. Botta, F. Corelli, Synthesis and biological investigation of S-aryl-S-DABO derivatives as HIV-1 inhibitors. Bioorg. Med. Chem. Lett. 16, 3541–3544 (2006)
V.J. Ram, Synthesis of pyrimidines and fused pyrimidines as leishmanicides and herbicides. J. prakt. Chemie 6, 893–905 (1989)
V.J. Ram, D.A.V. Berghe, A.J. Vlietinck, 5-Cyano-6-aryluracil and 2-thiouracil derivatives as potential chemotherapeutic agents. J. Heterocyclic Chem. 21, 1307–1312 (1984)
A.E. Rashad, A.E. Mahmoud, M.M. Ali, Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells. Eur. J. Med. Chem. 46, 1019–1026 (2011)
G.H. Sayed, M. El-Mobayed, A.G. El-Shekeil, E. Abd Elghani, A new route for the synthesis of tetrahydro and dihydro-3H-pyrazolo[3,4-c]pyridazino[4,3-e]pyridazine ring systems. Indian J. Chem. 29B, 72 (1990)
G.S. Waghmare, S.B. Junne, S.D. Shinde, A.S. Aghamare, S.V. Kuberkar, Synthesis and characterization of fused pyrimido-pyrimidine dicarbonitriles and their antibacterial activity. Chem. Sci. Trans. 2, 1–4 (2013)
T. Yakaiah, B.P.V. Lingaiah, B. Narsaiah, K.K. Pranay, U.S.N. Murthy, GdCl3 catalysed Grieco condensation: a facile approach for the synthesis of novel pyrimidine and annulated pyrimidine fused indazole derivatives in single pot under mild conditions and their anti-microbial activity. Eur. J. Med. Chem. 43, 341–347 (2008)
N. Zhang, S. Ayral-Kaloustian, T. Nguyen, R. Hernandez, C. Beyer, 2-Cyanoaminopyrimidines as a class of antitumor agents that promote tubulin polymerization. Bioorg. Med. Chem. Lett. 17, 3003–3005 (2007)
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Abdelghani, E., Said, S.A., Assy, M.G. et al. Heterocyclization of thiouracil derivative: synthesis of thiazolopyrimidines, tetrazolopyrimidines and triazolopyrimidines of potential biological activity. J IRAN CHEM SOC 12, 1809–1817 (2015). https://doi.org/10.1007/s13738-015-0656-2
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DOI: https://doi.org/10.1007/s13738-015-0656-2