Synthesis of Di and Tetraoximes from the Reaction of Phenylendiamines with Dichloroglyoxime

Document Type : Research Article

Authors

1 Department of Chemistry, Faculty of Science, University of Lorestan, Khorramabad, I.R. IRAN

2 Department of Biology, Faculty of Science, Tarbiat Modares University, Tehran, I.R. IRAN

Abstract

2,5,10,13-Tetraazatricyclo [12,2,2,26,9] icosa-1(16),6,8,14,17,19-hexene-3,4,11,12-tetraone tetraoxime (1a) and 2,5,11,14-tetraazatricyclo [13,3,1,16,10] icosa-1(19),6,8,10(20),15,17-hexaene-3,4,12,13-tetraonetetraoxime (1b) were obtained from condensation of 1,4- and 1,3-phenylendiamine with dichloroglyoxime, respectively. The reaction of 1,2-phenylendiamine with dichloroglyoxime resulted in the production of (2Z,3Z)-1,4-dihydroquinoxaline-2,3-dione dioxime (2). The x-ray structure determination of compound 2 shows the piprazine ring is rather planar relative to the fused aromatic ring. The results show that a resonance occurs between the aromatic ring and the C=N bond, through N4 and N3 atoms of the molecule. The results from x-ray data, indicated that the molecules 2 could exist as a dimmer by intermolecular hydrogen bonding between NH and OH groups.

Keywords

Main Subjects


[1] Kanno, H. and Yammamoto, H. European Patent, 0,636,605A1 (1994).
[2] Banks, C.V., Rec. Chem. Prog., 25, 85 (1964).
[3] Singh,  R.B.,  Garg,  B.S. and  Singh, R. P., Talanta, 26, 425 (1979).
[4] Ramadan, A.E., El-Mehasseb, I.M. and Isssa, R.M., Transition Met. Chem., 22, 529 (1997).
[5] Lance, K.A., Dzugan, S., Busch, D.H. and Alcock, N.W., Gazz. Chim. Ital., 126, 251 (1996).
[6] Schrauzer, G.N., Acc. Chem. Res., 1, 97 (1968).
[7] Tovrog, B.S., Kitko, D.J. and Drago, R.S., J. Am. Chem. Soc., 98, 5144 (1976).
[8] Boyer, J.H., Chem. Rev., 80, 495 (1980).
[9] Chakravorty, A., Coord. Chem. Rev., 13, 1 (1974).
[10] Schrauzer, G.N. and Kohnle, J., Chem. Ber., 97, 3056 (1964).
[11] Luneau,  D.,  Oshio,  H.,  Okawa, H. and Kida, S., Chem. Lett., 443 (1989).
[12] Grundman, G., Justus. Liebigs. Ann. Chem, 687, 191 (1965).
[13] Coburn, M, D., J. Heterocyclic. Chem. 5, 83 (1968).
[14] Greenwood, N. N.,  and Earnshaw, A., “Chemistry of the Elements”, pergamon press, oxford, 235 (1986).
[15] Sheldrick,    G.  M.,   SHELXTL   (1998 b)   v.  5.10, “Structure Determination Software Suite”, Bruker AXS, Madison, Wisconsin, USA.
[16] Willer, R., Moore, D. W., J. Org. Chem. 50, 5123 (1985).