Browse > Article
http://dx.doi.org/10.5012/jkcs.2016.60.4.245

An Improved Protocol on the Synthesis of Thiazolo[3,2-a]pyrimidine Using Ultrasonic Probe Irradiation  

Tan, Sian Hui (School of Marine Science and Environment, Universiti Malaysia Terengganu)
Chuah, Tse Seng (School of Food Science and Technology, Universiti Malaysia Terengganu)
Chia, Poh Wai (Institute of Marine Biotechnology, Universiti Malaysia Terengganu)
Publication Information
Abstract
An improved protocol on the synthesis of thiazolo[3,2-a]pyrimidine-6-carboxylate derivatives are reported. Previously, the thiazolo[3,2-a]pyrimidine-6-carboxylate derivatives were prepared in a two-step procedure. Under the improved procedure, the thiazolo[3,2-a]pyrimidine-6-carboxylate derivatives was readily prepared in a one-step reaction. This procedure was found to be more efficient than the previous protocol and also compared to the ultrasound bath and conventional heating methods in terms of yield and reaction time.
Keywords
One-pot three component synthesis; Thiazolo[3; 2-a]pyrimidine; Ultrasound; Solvent- and catalyst-free reaction;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
연도 인용수 순위
1 Balkan, A.; Uma, S.; Ertan, M.; Wiegrebe, W. Pharmazie 1992, 47, 687–688.
2 Tozkoparan, B.; Ertan, M.; Kelicen, P.; Demirdamar, R. Farmaco 1999, 54, 588–593.   DOI
3 Rida, S. M.; Habib, N. S.; Badawey, E. A.; Fahmy, H. T.; Ghozlan, H. A. Pharmazie 1996, 51, 927−931.
4 Duval, R.; Kolb, S.; Braud, E.; Genest, D.; Garbay, C. J. Comb. Chem. 2009, 11, 947–950.   DOI
5 Zhi, H.; Chen, L.; Zhang, L.; Liu, S.; Cheong, C. ARKIVOC 2008, 13, 266–277.
6 Wichmann, J.; Adam, G.; Kolczewski, S.; Mutel, V.; Woltering, T. Bioorg. Med. Chem. Lett. 1999, 9, 1573–1576.   DOI
7 Youssef, M. M.; Amin, M. A. Molecules 2012, 17, 9652–9667.   DOI
8 Sayed, H. H.; Shamroukh, A. H.; Rashad, A. E. Acta Pharm. 2006, 56, 231–244.
9 Sherif, S. M.; Youssef, M. M.; Mobarak, K. M. Tetrahedron 1993, 49, 9561–9572.   DOI
10 Domling, A.; Wang, W.; Wang, K. Chem. Rev. 2012,112, 3083-3135.   DOI
11 Lee, D.; Sello, J. K.; Schreiber, S.-L. Org. Lett. 2000,2, 709-712.   DOI
12 Ugi, I. Pure Appl. Chem. 2001, 73, 187–191.
13 Mehta, V. P.; Modha, S. G.; Ruijter, E.; Van Hecke, K.;Van Meervelt, L.; Pannecouque, C.; Balzarini, J.; Orru, R.V.; Van der Eycken, E. J. Org. Chem. 2011, 76, 2829-2839.
14 Liju, W.; Ablajan, K.; Jun, F. Ultrason. Sonochem.2015, 22, 113-118.   DOI
15 Mason, T. J. Chem. Soc. Rev. 1997, 26, 443–451.   DOI
16 Jiang, Y.; Chen, X.; Qu, L.; Wang, J.; Yuan, J.; Chen, S.; Li, X.; Qu, C. Ultrason. Sonochem. 2011, 18, 527–533.   DOI
17 He, J.-Y.; Xin, H.-X.; Yan, H.; Song, X.-Q.; Zhong, R.-G. Ultrason. Sonochem. 2011, 18, 466–469.   DOI
18 Wang, S. X.; Li, Z. Y.; Zhang, J. C.; Li, J. T. Ultrason. Sonochem. 2008, 15, 677–680.   DOI
19 Koufaki, M.; Fotopoulou, T.; Heropoulos, G. A. Ultrason. Sonochem. 2014, 21, 35–39.   DOI
20 Meshram, H. M.; Kumar, A. S.; Kumar, G. S.; Swetha, A.; Chennakesava, B.; Ramesh, P. Pharma Chemica 2012, 4, 956–960.
21 Zhao, B.; Jiang, L.-L.; Liu, Z.; Deng, Q.-G.; Wang, L.-Y.; Song, B.; Gao, Y. Heterocycles 2013, 87, 2093–2102.   DOI
22 Singh, B.; Guru, S. K.; Kour, S.; Jain, S. K.; Sharma, R.; Sharma, P. R.; Singh, S. K.; Bhushan, S.; Bharate, S. B.; Vishwakarma, R. A. Eur. J. Med. Chem. 2013, 70, 864–874.   DOI
23 Kotaiah, Y.; Krishna, N. H.; Raju, K. N.; Rao, C. V.; Jonnalagadda, S. B.; Maddila, S. J. Korean Chem. Soc. 2012, 56, 68–73.   DOI
24 Darehkordi, A.; Ghazi, S. Arab. J. Chem. 2015, 1–8.
25 Nagarajaiah, H.; Khazi, I. M.; Begum, N. S. Journal of Chemical Sciences 2012, 124, 847−855.   DOI
26 Batool, I.; Saeed, A.; Qureshi, I. Z.; Kalsoom, S.; Razzaq, A. Res. Chem. Intermed. 2016, 42, 1139−1163.   DOI
27 Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851-1854.
28 Dam, B.; Pal, A. K.; Gupta, A. Synth. Commun. 2016, 46, 275−286.   DOI
29 Koopmanschap, G.; Ruijter, E.; Orru,R. V. Beilstein J. Org. Chem. 2014, 10, 544-598.   DOI
30 Schreiber, S.-L. Science 2000, 287, 1964−1969.
31 Weber, L. Curr. Med. Chem. 2002, 9, 2085-2093.   DOI
32 Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Chem.Eur. J. 2009, 15, 1300-1308.   DOI
33 Ghosh, A. K. J. Org. Chem.2010, 75, 7967-7989.   DOI
34 Pando, O.; Stark, S.; Denkert,A.; Porzel, A.; Preusentanz, R.; Wessjohann, L. A. J. Am.Chem. Soc. 2011, 133, 7692-7695.   DOI
35 Ghahremanzadeh, R.; Rashid, Z.; Zarnani, A.-H.; Naeimi,H. J. Ind. Eng. Chem. 2014, 20, 4076-4084.   DOI
36 Rouhani, M.; Ramazani, A.; Joo,S. W. Ultrason. Sonochem. 2015, 22, 391-396.   DOI