ZnO-NR as the efficient catalyst for the synthesis of new thiazole and cyclopentadienone phosphonate derivatives in water
Corresponding Author
Zinatossadat Hossaini
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Correspondence
Zinatossadat Hossaini, Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran.
Email: [email protected]
Fatemeh Sheikholeslami-Farahani, Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran.
Email: [email protected]
Search for more papers by this authorDaryoush Zareyee
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Search for more papers by this authorCorresponding Author
Fatemeh Sheikholeslami-Farahani
Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran
Correspondence
Zinatossadat Hossaini, Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran.
Email: [email protected]
Fatemeh Sheikholeslami-Farahani, Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran.
Email: [email protected]
Search for more papers by this authorSamaneh Vaseghi
Kosar Public School, Education of Mazandaran Province, Sari, Iran
Search for more papers by this authorAfshin Zamani
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Search for more papers by this authorCorresponding Author
Zinatossadat Hossaini
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Correspondence
Zinatossadat Hossaini, Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran.
Email: [email protected]
Fatemeh Sheikholeslami-Farahani, Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran.
Email: [email protected]
Search for more papers by this authorDaryoush Zareyee
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Search for more papers by this authorCorresponding Author
Fatemeh Sheikholeslami-Farahani
Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran
Correspondence
Zinatossadat Hossaini, Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran.
Email: [email protected]
Fatemeh Sheikholeslami-Farahani, Firoozkooh Branch, Department of Chemistry, Islamic Azad University, Firoozkooh, Iran.
Email: [email protected]
Search for more papers by this authorSamaneh Vaseghi
Kosar Public School, Education of Mazandaran Province, Sari, Iran
Search for more papers by this authorAfshin Zamani
Qaemshahr Branch, Department of Chemistry, Islamic Azad University, Qaemshahr, Iran
Search for more papers by this authorAbstract
Functionalized thiazoles are generated from the reaction of dimethyl acetylenedicarboxylate, benzoylisothiocyanates, and primary amines and trialkyl phosphite in the presence of ZnO-nanorods as the catalyst in water. Also, a series of polysubstituted cyclopentadienone phosphonate derivatives were synthesized via one-pot multicomponent reactions of primary amines and phosphites with activated acetylenic compounds in water as the solvent at room temperature. Particularly valuable features of this method include high yields of products, broad substrate scope, short reaction time, and straightforward procedure.
References
- 1A. Dömling, Chem. Rev. 2006, 106, 17.
- 2C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51.
- 3J. Zhu, Eur. J. Org. Chem. 2003, 2003, 1133.
- 4A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 2000, 39, 3168.
10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 5J. Zhu, H. Bienayme’, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany 2005.
10.1002/3527605118 Google Scholar
- 6T. Ngouansavanh, J. Zhu, Angew. Chem. Int. Ed. 2007, 46, 5775.
- 7E. K. Laurent, M. Gizolme, L. Grimaud, J. Oble, Org. Lett. 2006, 8, 4019.
- 8P. A. Tempest, Curr. Opin. Drug Discov. 2005, 8, 776.
- 9K. Lu, T. Luo, Z. Xiang, Z. You, R. Fathi, J. Chen, Z. Yang, J. Comb. Chem. 2005, 7, 958.
- 10J. R. Lewis, Nat. Prod. Rep. 1996, 13, 435.
- 11T. J. Kealy, P. L. Pauson, Nature 1951, 168, 1039.
- 12G. Wilkinson, F. G. Stone, E. W. Abel, Comprehensive Organometallic Chemistry, Pergamon, Oxford 1982, 3–7.
10.1016/B978-008046518-0.00067-2 Google Scholar
- 13U. Siemeling, Chem. Rev. 2000, 100, 1495.
- 14H. Butenschön, Chem. Rev. 2000, 100, 1527.
- 15A. D. Allen, T. T. Tidwell, Chem. Rev. 2001, 101, 1333.
- 16V. Nair, R. S. Menon, P. B. Beneesh, V. Sreekumar, S. Bindu, Org. Lett. 2004, 6, 767.
- 17A. Gutnov, B. Heller, H. J. Drexler, A. Spannenberg, G. Oehme, Organometallics 2003, 22, 1550.
- 18O. T. Beachley, D. J. MacRae, M. R. Churchill, A. Y. Kovalevsky, E. S. Robirds, Organometallics 2003, 22, 3991.
- 19T. Jikyo, M. Eto, K. Harano, J. Chem. Soc. Perkin Trans. 1998, 1, 3463.
- 20(a) A. Gamba, R. Gandolfi, R. Oberti, N. Sardone, Tetrahedron 1993, 49, 6331. (b) T. Kawase, T. Ohsawa, T. Enomoto, M. Oda, Chem. Lett. 1994, 1994, 1333. (c) U. Kumar, T. X. Neenan, Macromolecules 1995, 28, 124. (d) T. Shibata, T. Ohta, K. Soai, Tetrahedron Lett. 1998, 39, 5785. (e) T. Jikyo, M. Eto, K. Harano, Tetrahedron 1999, 55, 6051.
- 21(a) J. J. Eisch, A. A. Aradi, K. I. Han, Tetrahedron Lett. 1983, 24, 2073. (b) L. Garlaschelli, M. C. Malatesta, S. Panzeri, A. Albinati, F. Ganazzoli, Organometallics 1987, 6, 63. (c) A. J. Pearson, R. J. Shively Jr., R. A. Dubbert, Organometallics 1992, 11, 4096. (d) K. Kirchner, K. Mereiter, A. Umfahrer, R. Schmid, Organometallics 1994, 13, 1886. (e) H.-J. Knolker, E. Baum, J. Heber, Tetrahedron Lett. 1995, 36, 7647.
- 22R. Roers, F. Rominger, C. Braunweiler, R. Gleiter, Tetrahedron Lett. 1998, 39, 7831.
- 23G. Zadel, E. Breitmaier, Angew. Chem. Int. Ed. Engl. 1992, 31, 1035.
- 24(a) R. Breslow, Acc. Chem. Res. 1991, 24, 159. (b) C. J. Li, T. H. Chang, Organic Reactions in Aqueous Media, Wiley, New York 1997, 1–199. (c) U. M. Lindstrm, Chem. Rev. 2002, 102, 2751. (d) K. Shu, M. Kei, Acc. Chem. Res. 2002, 35, 209. (e) C. J. Li, Chem. Rev. 2005, 105, 3095. (f) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. Int. Ed. 2005, 44, 3275. (g) M. C. Pirrung, Chem. Eur. J. 2006, 12, 1312. (h) V. Polshettiwar, R. S. Varma, Acc. Chem. Res. 2008, 41, 629.
- 25(a) M. A. Mironov, QSAR Comb. Sci. 2006, 25, 423. (b) A. Dömling, Chem. Rev. 2006, 106, 17. (c) D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602. (d) R. V. A. Orru, M. de Greef, Synthesis 2003, 2003, 1471.
- 26M. Sabbaghan, A. A. Firooz, V. J. Ahmadi, J. Mol. Liq. 2012, 175, 135.
- 27I. Yavari, S. Souri, M. Sirouspour, Synlett 2008, 11, 1633.
- 28Z. S. Hossaini, F. Rostami-Charati, M. Ghasemian, S. A. S. Abad, Synlett 2015, 26, 1222.
- 29M. A. Khalilzadeh, A. Hasanni, M. M. Baradarani, Z. S. Hossaini, Chin. Chem. Lett. 2011, 22, 49.
- 30Z. S. Hossaini, F. Sheikholeslami-Farahani, F. Rostami-Charati, Comb. Chem. High Throughput Screen. 2014, 17, 804.
- 31S. Seyfi, F. Rostami-Charati, Z. S. Hossaini, M. R. Zardoost, Lett. Org. Chem. 2014, 11, 409.
- 32Z. S. Hossaini, F. Rostami-Charati, M. E. Moghadam, F. Moghaddasi-Kochaksaraee, Chin. Chem. Lett. 2014, 25, 794.
