Rizk Elsayed KHIDRE, Wafaa Mahmoud ABDOU

Wittig{Horner reagents: powerful tools in the synthesis of 5-and 6-heterocycliccompounds; shedding light on their application in pharmaceutical chemistry

This paper reviews literature over 25 years' activity on phosphoryl carbanion reagents and shows that thesecompounds are powerful tools in organic chemistry. The main target of this review is to outline some of the reactivepeculiarities that make this class of compounds powerful tools in the synthesis of 5- and 6-heterocyclic compounds and/orsubstituted heterocycle phosphor esters. The importance of these latter compounds in pharmacology is also discussed.

PDF

___

1.Wardle, N. J.; Bligh, S. W. A.; Hudson, H. R.Curr. Org. Chem.2005,9, 1803-1828.
2.Manier, M. L.; Hachey, D. L.; Bachmann, B. O.Org. Lett.2005,7, 2763-2765.
3.Seto, H.; Kuzuyama, T.Nat. Prod. Rep.1999,16, 589-596.
4.Fields, S. C.Tetrahedron1999,55, 12237-12273.
5.Franco, S.; Melendez, E.; Merchan, F. L.J. Heterocycl. Chem.1995,32, 1181-1183.
6.Muruganantham, R.; Mobin, S. M.; Namboothiri, I. N. N.Org. Lett.2007,9, 1125-1128.
7.Konovets, A. I.; Kostyuk, A. N.; Pinchuk, A. M.; Tolmachev, A. A.; Fischer, A.; Jones, P. G.; Schmutzler, R.Heteroat. Chem.2003,14, 452-458.
8.Tolmachev, A. A.; Sviridon, A. I.; Kostyuk, A. N.; Pinchuk, A. M.Heteroat. Chem.1995,6, 449-459.
9.Abdel-Wahab, B. F.; Khidre, R. E.Turk. J. Chem.2014,38, 1-27.
10.Khidre, R. E.; Abdel-Wahab, Bakr F.Turk. J. Chem.2013,37, 1-27.
11.Abdou, W. M.; Khidre R. E.Curr. Org. Chem.2012,16, 913-930.
12.Abdel-Wahab, B. F.; El-Mansy, Khidre, R. E.J. Iran. Chem. Soc.2013,10, 1085-1102.
13.Abdou, W. M.; Barghash, R. F.; Khidre, R. E.Monatsh. Chem.2013,144, 1233-1242
14.Abdel-Wahab, B. F.; Khidre, R. E.J. Chem.2013, Article ID 851297.
15.Albrecht, A.; Kedzia, J.; Koszuk, J. F.; Warzycha, E.; Janecki, T.Tetrahedron Lett.2006,47, 2353-2355.
16.Davis, F.A.; Wu, Y.; Xu, H.; Zhang, J.Org. Lett.2006,8, 2273-2276.
17.Mikolajczyk, M.; Krysiak, J. A.; Midura, W. H.; Wieczorek, M. W.; Rozycka-Sokolowska, E.J. Org. Chem.2006,71, 8818-8823.
18.Kamel, A. A.Phosphorus, Sulfur Silicon Relat. Elem.2007,182, 765-777.
19.Ferris, L.; Haigh, D. Moody, C. J.J. Chem. Soc., Perkin Trans. 11996, 2885-2888.
20.Brown, J. A.Tetrahedron Lett.2000,41, 1623-1626.
21.Broekhof, N. L. J. M.; van Elburg, P.; Hoff, D. J.; van der Gen, A. Recueil des Travaux Chimiques des Pays-Bas1984, 103, 317-321.
22.Langlois, N.; Radom, M. O.Tetrahedron Lett.1998,39, 857-860.
23.Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Rodriguez, M.; Martos, A.Tetrahedron2006,62, 6006-6011.
24.Izquierdo, I.; Plaza, M. T.; Franco, F.Tetrahedron: Asymmetry2004,15, 1465-1469.
25.Robins, D. J.Nat. Prod. Rep.1995;12, 413-418:
26.Abdou, W. M.; Salem, M. A. I.; Barghash, R. F.Synth. Commun.2003,33, 1341-1357.
27.Abdou, W. M.; Kamel, A. A.; Shaddy, A. A.Eur. J. Med. Chem.2010,45, 5217-5224.
28.Abdou, W. M.; Khidre, M.D. Kamel, A. A.; Awad, G. E. A.Monatsh. Chem.2014,145, 675-682.
29.Khusainova, N. G.; Irtuganova, E. A.; Pudovik A. N.Russ. J. Gen. Chem.2001,71, 337-338.
30.Abdou, W. M.; Khidre, M. D.; Khidre, R. E.Eur. J. Med. Chem.2009,44, 526-532.
31.Chen, H.; Qian, D.; Xu, G.; Liu, Y.; Chen, X.; Shi, X.; Cao, R.; Liu, L.Synth. Commun.1999,29, 4025-4033.
32.Akacha, A. B.; Ayed, N.; Baccar, B.; Charrier, C.Phosphorus, Sulfur, Silicon Relat. Elem.1988,40, 63-68.
33.Hassen, Z.; Akacha, A. B.; Hajjem, B.Phosphorus, Sulfur, Silicon Relat. Elem.2003,178, 2349-2356.
34.Barghash, R. F.; Ganoub, N. A.; Abdou, W. M.Monatsh. Chem.2014,145, 1621-1630.
35.Armstrong, S. K.; Warren, S.; Collington, E. W.; Nayler, A.Tetrahedron Lett.1991,32, 4171-4174.
36.Armstrong, S. K.; Collington, E. W.; Knight, J. G.; Naylorb, A.; Warren, S.J. Chem. Soc., Perkin Trans. 11993,13, 1433-1447.
37.Abdou, W. M.; Sediek, A. A.; Khidre, M. D.Monatsh. Chem.2008,139, 617-623.
38.Abdou, W. M.; Salem, M. A. I.; El-Khoshnieh, Y. O.; Barghash, R. F.Synlett.2002,9, 1417-1422.
39.Abdou, W. M.; Salem, M. A. I.; Barghash, R. F.Arkivoc2007,xv, 45-60.
40.Abdou, W. M.; Khidre, M. D.Phosphorus, Sulfur and Silicon2004,179, 1307-1322.
41.Liu, F.; Palmer, D. C.; Sorgi, K. L.Tetrahedron Lett.2004,45, 1877-1880.
42.Mohamed, N. R.; El-Saidi, M. M. T.; Hassaneen, H. M.; Erian, A. W.Phosphorus, Sulfur Silicon Relat. Elem.2004,179, 521-528.
43.Abdou, W. M.; Ganoub, N. A.; Sabry, E.Acta Pharm.2014,64, 267-284.
44.Koldobskii, A. B.; Solodova, E. V.; Godovikov, I. A.; Verteletskii, P. V.; Kalinin, V. N.J. Fluorine Chem.2010,131, 873-878.
45.Arimitsu, S.; Konno, T.; Gupton, J. T.; Ishihara, T.; Yamanaka, H.J. Fluorine Chem.2006,127, 1235-1241.
46.Arsanious, M. N.; Maigali, S. S.; Boulos, L. S.Int. J. Chem. Tech. Res.2013,5, 2003-2010.
47.Guillaume, M.; Janousek, Z.; Viehe, H. G.Synthesis1995,8, 920-922.
48.Palacios, F.; Ochoa de Retana, A. M.; Pascual, S.; Lopez de Munain, R.; Oyarzabal, J.; Ezpeleta, J. M.Tetrahedron2005,61, 1087-1094.