An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions

KÜÇÜKİSLAMOĞLU, MUSTAFA; Zengin, Mustafa; Arslan, Mustafa; NEBİOĞLU, MEHMET; Beşoluk, Şenol

An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions

Şenol BEŞOLUK, (Sakarya Üniversitesi, Eğitim Fakültesi, Sakarya, Türkiye)

Mustafa KÜÇÜKİSLAMOĞLU, (Sakarya Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Sakarya, Türkiye)

Mustafa ZENGİN, (Sakarya Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Sakarya, Türkiye)

Mustafa ARSLAN, (Sakarya Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Sakarya, Türkiye)

Mehmet NEBİOĞLU (Sakarya Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Sakarya, Türkiye)

Turkish Journal of Chemistry

1 0

Yıl: 2010 Cilt: 34 Sayı: 3 Sayfa Aralığı: 411 - 416 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions

Öz:

A simple, efficient, and practical procedure for the Biginelli reaction using zirconium hydrogen phosphate [Zr$(H _2PO _4) - _2 $] as a novel solid acid catalyst is described under solvent-free conditions in high yields. The catalyst exhibited remarkable reactivity and it is reusable.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. a) Kappe, C. O. Tetrahedron 1993, 49, 6937-6963; b) Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803-2816; (c) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888.
2. a) Kappe, O. C., Eur. J. Med. Chem., 2000, 35, 1043-1052; b) Stefani, H. A.; Oliveira, C. B.; Almeida, R. B.; Pereira, C. M. P.; Braga, R. C.; Cella, R., Borges, V. C.; Savegnago, L.; Nogueira C. W. Eur. J. Med. Chem., 2006, 41: 513-518; c) Blackburn, C.; Guan, B.; Brown, J.; Cullis, C.; Condon, S. M.; Jenkins, T. J; Peluso, S.; Ye, Y. C.; Gimeno, R. E.; Punreddy, S.; Sun,Y.; Wu, H.; Hubbard, B.; Kaushik, V.; Tummino, P.; Sanchetti, P.; Sun, D. Y.; Daniels, T.; Tozzo, E.; Balani; S. K.; Raman, P. Bioorg. Med. Chem. Lett., 2006, 16, 3504-3509.
3. Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Browse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Bren, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182-1188.
4. Biginelli, P. Gazz. Chem. Ital. 1893, 23, 360-413.
5. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.; Reddy, V. V. N. Tetrahedron Lett. 2002, 43, 2657-2659.
6. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270-6276.
7. Kunar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C. D. Tetrahedron Lett. 2001, 42, 7873-7875.
8. Sun, Q.; Wang, Y.; Ge, Z.; Cheng, T.; Li, R. Synthesis 2004, 1047-1051.
9. Zhu, Y. L.; Pan, Y. J.; Huang, S. L. Synthetic Commun. 2004, 34, 3167-3174.
10. Choudhary, V. R.; Tillu, V. S.; Borate, H. B.; Wakharkar, R. D. Catal. Comm. 2003, 4, 449-453.
11. Zheng, R. W.; Wang, X. X.; Xu, H.; Du, J. X. Synthetic Commun. 2006, 36, 1503-1513.
12. Varma, R. S.; Green Chemistry 1999, 43-55.
13. Corma, A. Curr. Opin. Solid St. M. Sci. 1997, 2, 63-75; Okuhara, T. Chem. Rev. 2002, 102, 3641-3666.
14. a) Costa, M. C. C.; Johnstone, R. A. W.; Whittaker, D. J. Mol. Catal. A 1998, 129, 79-89; b) Costa, M. C. C.; Hodson, L. F.; Johnstone, R. A. W.; Liu J.; Wittaker, D. J. Mol. Catal. A 1999, 142, 349-360; c) Marcu, I. C.; Sandulescu I.; Millet, J. M. J. Mol. Catal. A: Chem. 2003, 203, 241-250; d) Clearfield A.; Takur, T. S. J. Catal. 1980, 65, 185-194; e) Segawa, K.; Kurusu, Y.; Nakajima Y.; Kinoshita, M. J. Catal. 1985, 94, 491-500; f) La Ginestra, A.; Partono, P.; Berardelli, M. L.; Galli, P.; Ferragina, C.; Massucci, M. A. J. Catal. 1987, 103, 346-356; g) Constantino, U.; Fringuelli, F.; Orru, M.; Nocchetti, M.; Piermatti, O.; Pizzo, F. Eur. J. Org. Chem. 2009, 1214-1220.
15. Kamiya, Y.; Sakata, S.; Yoshinaga, Y.; Ohnishi, R.; Okuhara, T. Catal. Lett. 2004, 94, 45-47.
16. a) Kucukislamoglu, M.; Nebioglu, M.; Zengin, M.; Arslan, M.; Yayli, N. J. Chem. Res. 2005, 556-560; b) Besoluk, S.; Kucukislamoglu, M.; Nebioglu, M.; Zengin, M.; Arslan, M. J. Iran. Chem. Soc. 2008, 5, 62-66; c) Arslan, M.; Faydali, C.; Zengin, M.; Kucukislamoglu, M.; Demirhan, H. Turk. J. Chem. 2009, 33, 769-774.
17. Salehi, P.; Dabiri, M.; Zolfigol, A. M.; Fard, B. A. M. Tetrahedron Lett. 2003, 44, 2889-2891.
18. Fu, Y. N.; Yuan, F. Y.; Zhong, C.; Wang, W. S.; Wang, T. J.; Pepe, C. Tetrahedron 2002, 58, 4801-4807.
19. Bose, K. A.; Manhas, S. M.; Pednekar, S.; Ganguly, N. S.; Dang, H.; He, W.; Mandidi, S. P. A. Tetrahedron Lett. 2005, 46, 1901-1903.
20. Reddy, R. K.; Reddy, V. C.; Mahesh, M.; Raju, K. V. P.; Reddy, N. V. V. Tetrahedron Lett. 2003, 44, 8173-8175.
21. Tu, S.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y.; Shi, D.; Wang, X. S. Tetrahedron Lett. 2003, 44, 6153-6155.
22. Li, T. J.; Han, F. J.; Yang, H. J.; Li, S. T. Ultrason. Sonochem. 2003, 10, 119-122.
23. Yarim, M.; Sarac, S.; Ertan, M.; Batu, S. O.; Erol, K. Il Farmaco 1999, 54, 359-363.
24. Singh, K.; Singh, J.; Deb, P. K.; Singh, H. Tetrahedron 1999, 55, 12873-12880.
25. Joseph, J. K.; Jain, S. L.; Sain, B. J. Mol. Catal. A: Chem. 2006, 247, 99-102.

APA	Beşoluk Ş, KÜÇÜKİSLAMOĞLU M, Zengin M, Arslan M, NEBİOĞLU M (2010). An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. , 411 - 416.
Chicago	Beşoluk Şenol,KÜÇÜKİSLAMOĞLU MUSTAFA,Zengin Mustafa,Arslan Mustafa,NEBİOĞLU MEHMET An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. (2010): 411 - 416.
MLA	Beşoluk Şenol,KÜÇÜKİSLAMOĞLU MUSTAFA,Zengin Mustafa,Arslan Mustafa,NEBİOĞLU MEHMET An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. , 2010, ss.411 - 416.
AMA	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. . 2010; 411 - 416.
Vancouver	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. . 2010; 411 - 416.
IEEE	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M "An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions." , ss.411 - 416, 2010.
ISNAD	Beşoluk, Şenol vd. "An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions". (2010), 411-416.

APA	Beşoluk Ş, KÜÇÜKİSLAMOĞLU M, Zengin M, Arslan M, NEBİOĞLU M (2010). An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. Turkish Journal of Chemistry, 34(3), 411 - 416.
Chicago	Beşoluk Şenol,KÜÇÜKİSLAMOĞLU MUSTAFA,Zengin Mustafa,Arslan Mustafa,NEBİOĞLU MEHMET An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. Turkish Journal of Chemistry 34, no.3 (2010): 411 - 416.
MLA	Beşoluk Şenol,KÜÇÜKİSLAMOĞLU MUSTAFA,Zengin Mustafa,Arslan Mustafa,NEBİOĞLU MEHMET An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. Turkish Journal of Chemistry, vol.34, no.3, 2010, ss.411 - 416.
AMA	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. Turkish Journal of Chemistry. 2010; 34(3): 411 - 416.
Vancouver	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions. Turkish Journal of Chemistry. 2010; 34(3): 411 - 416.
IEEE	Beşoluk Ş,KÜÇÜKİSLAMOĞLU M,Zengin M,Arslan M,NEBİOĞLU M "An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions." Turkish Journal of Chemistry, 34, ss.411 - 416, 2010.
ISNAD	Beşoluk, Şenol vd. "An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions". Turkish Journal of Chemistry 34/3 (2010), 411-416.