Free accessResearch articleFirst published online 2004-8
2,6-Bis [3-N,N-Dimethylamino-1-Oxopropen-1-Yl]Pyridine as a Building Block in Heterocyclic Synthesis: Synthesis of 2,2′:6′,2″-Terpyridines and 2,6-Bis[Pyrazolyl,Isoxazolyl,Diazepinyl,Pyrazolo[5,1-a]Pyrimidinyl and Pyrazolo-[4,3-D]Pyridazinyl]Pyridines
A convenient synthesis is reported of some new 2, 2′:6′, 2″-terpyridines, and polycyclic pyridino-2,6-bis-[heterocycles and fused heterocycles] via reaction of 2,6-bis[3-N,N-dimethylamino-1-oxopropen-1-yl]pyridine (2) with various type of nucleophilic reagents. The biological screening showed that many of the prepared compounds have good antibacterial and antifungal activities comparable to Ampicillin and clotrimazoles.
LahausG., and DittmarW., S. Africa Patent, 6 906036: C.A. 1988, 73, 720308.
2.
YoungdaleG.A., U.S. Patent, 4288 440; C. A. 1982, 96, 6596c.
3.
DorigoP., GaionR. M, BellucoP., FraccarolloD., MaragnoI., BombieriG., BenelolloF., MostilL., and OrsiniF., J. Med. Chem., 1993, 36, 2475.
4.
DolleV., NguyenE. C. H., AubertinA. M., KirnA., AndreolaM. L., JamiesonG., Tarrago-LitvakL., and BisagniE., J. Med. Chem., 1995, 38, 4679.
5.
GhozlanS.A. S., and HassanienA. A., Tetrahedron, 2002, 58, 9423.
6.
HassanienA.A., and GhozlanS. A. S., and El-NagdiM. H., J. Heterocyclic Chem., 2003, 40, 225.
7.
ErianA.W., HassanienA. A., and MohamedN. R., Phosphorus, Sulfur Silicon, 1999, 155, 147.
8.
HassanienA.A., Abdel HafizI. S., and El-NagdiM. H., J. Chem. Res. (S), 1999, 8, (M), 129.
9.
HassanienA.A., AFINIDAD J., 2003, 60, 468.
10.
BejanE., Ait HaddouH., DaranJ. C., and BalavoineG. G. A.Synthesis, 1996, 1012.
11.
BejanE., HaddouH. Ait, DaranJ. C., and BalavoineG. G. A., Eur. J. Org. Chem., 1998, 2907, F. Pezet, L. Routaboul, J.C. Daran, I. Sasaki, H. Ait. Haddou and G.G.A. Balavoine, Tetrahedron, 2000, 56, 8489.
12.
TerentA.P., RukhadzeE. G., MochalinaI. G., and RodeV. V., Zhur. Vsesoyuz. Khim Obshchestva im. D.I. Mendeleeva1961, 6, No. 1, 116. C. A., 1961, 55, 144450i
13.
ConstableE.C., Adv. Inorg. Chem. Radiochem.1986, 30, 69. E.C. Constable, A.M.W. Cargill Thompson and D.A. Tocher in Supramolecular Chemistry, ed. V. Balzani and Kluwer Dortrecht, 1992, p.219; Cargill Thompson A.M.W Coord. Chem. Rev., 1997, 160, 1.
14.
LinY-i., and LangS. A.Jr., J. Heterocyclic Chem., 1977, 14, 345.
15.
DomiguezE., IbeasE., MarigortaE. A.; PalaciosJ. K., and SanMartinR., J. Org. Chem., 1996, 61, 5435.
16.
PleierA.K., GlasH., GroscheM., SirschP., and ThielW. R., Synthesis, 2001, 1, 55.
17.
Al-MousawiS.M., MohammadM. A., and ElnagdiM. H., J. Heterocyclic Chem., 2001, 38, 989.
18.
ElnagdiM.H., Abd-ElaalF. A., and ElgemeieG. E. H., Heterocycles, 1985, 23, 3121 and references cited therein