Iminophosphoranes in Heterocyclic Synthesis: A Facile Synthesis of Pyrido[4,3-D]Pyrimidine and Pyrido[4,3-D][1,3]Oxazine Derivatives via Intermolecular aza-Wittig Reactions
Omran A. Omran
Chemistry Department, Faculty of Science, Sohag University, 82524 Egypt
College of Science in Zulfi, P. O. Box 1712, Majmaah University, 11932 Saudi Arabia
Search for more papers by this authorSamia M. Sayed
Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
Search for more papers by this authorCorresponding Author
Mohamed A. Raslan
Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
E-mail: [email protected]Search for more papers by this authorOmran A. Omran
Chemistry Department, Faculty of Science, Sohag University, 82524 Egypt
College of Science in Zulfi, P. O. Box 1712, Majmaah University, 11932 Saudi Arabia
Search for more papers by this authorSamia M. Sayed
Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
Search for more papers by this authorCorresponding Author
Mohamed A. Raslan
Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
E-mail: [email protected]Search for more papers by this authorAbstract
A novel series of pyrido[4,3-d]pyrimidine and pyrido[4,3-d][1,3]oxazine derivatives were synthesized via tandem aza-Wittig and annulation reactions with the corresponding iminophosphoranes, aromatic isocyanate, and amines. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis.
References and Notes
- 1Numazl, H.; Mirzeni, Y. R.; Azamat, H. J Heterocycl Chem 2001, 38, 1051.
- 2Haggarty, S. R.; Mayer, T. U.; Miyamoto, D. T.; Fathi, R.; King, R. W.; Mitchison, T. J.; Schreiber, S. L. Chem Biol 2000, 7, 275.
- 3Thirumurugan, P.; Mahslsxmi, S.; Perumal, P. J Chem Sci 2010, 122, 819.
- 4Ghosh, N. N.; Kiskan, B.; Yagci, Y. Prop Polym Sci 2007, 32, 1344.
- 5Tomasulo, M.; Sortino, S.; Raymo, F. M. Org Lett 2005, 7, 1109.
- 6Chylinska, J. B.; Janowiec, M.; Urbanski, T. Brit J Pharmacol 1971, 43, 649.
- 7Madauss, K. P.; Stewart, E. L.; Williams, S. P. Med Res Rev 2007, 27, 474.
- 8Duffin, M.; Rollo, I. M. Brit J Pharmacol 1957, 12, 171.
- 9Chylinska, J. B.; Urbanski, T. J Med Chem 1963, 6, 484.
- 10Cocuzza, A. J.; Chidester, D. R.; Cordova, B. C.; Jeffrey, S.; Parsons, R. L.; Bacheler, L. T.; Erickson-Viitanen, S.; Trainor, G. L.; Ko, S. S. Biorg Med Lett 2001, 11, 1177.
- 11Liu, H. F.; Ji, M.; Cai, J. Arch Pharm Chem Life Sci 2006, 339, 675.
- 12Butler, J. D.; Solano, D. M.; Robins, L. I.; Haddadin, M. J.; Kurth, M. J. J Org Chem 2008, 73, 234.
- 13Vrouenraets, S. M. E.; Wit, F. W. N. M.; Van-Tongreen, J.; Lange, J. M. A. Expert Opin Pharmacother 2007, 8, 851.
- 14Rewcastle, W. G.; Palmer, D. B.; Thompson, A. M.; Bridges, A. J.; Cody, D. R. J Med Chem 1996, 39, 1823.
- 15Heckler, R. E.; Jourdan, G. P. Eur Patent 1991, 414, 386.
- 16Takeuchi, H.; Yanagida, S.; Ozaki, T.; Hagiwara, S.; Eguchi, S. J Org Chem 1989, 54, 431.
- 17Eguchi, S.; Goto, S. Heterocycl Commun 1994, 1, 51.
- 18Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523.
- 19Eguchi, S. Top Heterocycl Chem 2006, 6, 113.
- 20Okawa, T.; Toda, M.; Eguchi, S.; Kakehi, A. Synthesis 1998 1467.
- 21(a) Molina, P.; Fresneda, P. M. J Chem Soc Chem Commun 1819, 1988; (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1990, 46, 1063.
- 22Boschelli, D. H.; Wu, Z.; Klutchko, S. R.; Showalter, H. D. H.; Hamby, J. M.; Lu, G. H.; Major, T. C.; Dahring, T. K.; Batley, B.; Panek, R. L.; Keiser, J.; Hartl, B. G.; Kraker, A. J.; Klohs, W. D.; Roberts, B. J.; Patmore, S.; Elliott, W. L.; Steinkampf, R.; Bradford, L. A.; Hallak, H.; Doherty, A. M. J Med Chem 1998, 41, 4365.
- 23(a) Rosowsky, A.; Chen, H. J Org Chem 2001, 66, 7522; (b) DeGraw, J. I.; Christie, P. H.; Colwell, W. T.; Sirotnak, F. M. J Med Chem 1992, 35, 3204.
- 24Ren, Q.; Shi, Y.; Gu, Y.; Li, B.; He, H. J Heterocycl Chem 2014, 51, 285.
- 25Raslan, M.; Khalil, M.; Sayed, S. Heterocycles 2013, 87, 2567.
- 26Sayed, S. M.; Khalil, M. A.; Raslan, M. A. Eur J Chem 2014, 5, 356.
- 27Zahi, Y.; Shi, D.-Q. J Heterocycl Chem 2013, 50, 1039.
- 28Appel, R.; Kleistuk, R.; Ziehn, K. D.; Knoll, F. Chem Ber 1970, 103, 3631.
- 29Wamhoff, H.; Herrmann, S.; Stoelben, S.; Nieger, N. Tetrahedron 1993, 49, 581.
- 30Wamhoff, H.; Richardt, G.; Stoelben, S. Adv Heterocycl Chem 1993, 64, 159.
10.1016/S0065-2725(08)60172-5 Google Scholar
- 31Barsy, M. A.; El Rady, E. A.; Ismael, M. A. J Heterocycl 2012, 49, 388.
