Document Type : Research Paper

Authors

1 University of Anbar - College of Science

2 University of Anbar - College of Education for women

10.37652/juaps.2009.15365

Abstract

:- Z)-2- ((2-hydroxybenzylideneamino)methyl -2 -(hydroxy)propane -1,3-diol,)E) -4- (3-hydroxy-2,2-bis (hydroxyl methyl) propylimino)pentan-2-one, -2- ((4-(hydrazonopentane -2-ylideneamino methyl)-2 -(hydroxyl methyl)propane-1,3-diol and (Z)-2-((4-amino-1,5-dimethyl-2-phenyl-1H –pyrazol-3(2H)-ylideneamino)methyl)-2-(hydroxymethyl)propane-1,3-diol were prepared by condensation of 2-(aminomethyl)-2-(hydroxymethyl)propane-1,3-diol with 2-hydroxy benzaldehyde, pentane-2,4-dione, (E)-4-hydrazonopentan-2-one and 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one .These Schiff- bases were reacted with Succinic, Maleic and Malonic anhydride in absolute ethanol to give 6,7-membered heterocyclic ring system Oxazepine,Oxazepane,Oxazinan.The Schiff-bases and the final products were identified by their melting points, elemental analysis, FT-IR and UV-Visible spectra.

Keywords

Main Subjects

[1]-Toshio Makai, Tsutomu Kumagai, and Osamu Sashimoto1977, (photochemical and thermal reactions of some heterocycles containing C=N-O and N=C-O group) Pure and Appl.  Chem.Vol.49,pp.287-308
 [2]- Cheesman,G.W.H.and Greenberg ,S.G. 1979, (Synthesis of 5,6-dihydro-4H- pyrrolo[1,2-α] [1,4] benzodiazepines), J. Heterocyclic Chem. 16,241 
[3]- Schiff ,H.. 1864,Ann, 131,118
[4]- Clifford J. Crewell, Olaf, A. Rungvist, and Malcolm M. Campbell 1972, ( Spectral analysis of organic compounds),2nd ed., Longman.                 
[5] J. Macmillan, S.Washburen, J. HeterocyclicChem.,Vol.1, No.6, (1975) pp.1215.  
[6] J. H. Macmillan.,OrganicPreparation proceed. Int.,Vol.9,No.2,(1977) ,pp.87.
[7] H.Uchida, H Iwasawa,.and M.Ohta,Synthesis and cycloaddition reaction of 1,3- oxazepine, Chem.Soc.Jpn.,Vol.46,No.1,(1 973) ,pp. 3277 .         
[8] T,Kato  and M. Kando, Synthesis and cycloaddition reaction of di and tri-       substituted-1,3-oxazepine, Hetrocycles,Vol.1,No.3,(1975),pp.927
 [9] R. N.Lacey, Thermal Rearrangement of Tetraphenyl-(Z)- ketovinylazirine      J.Chem. Soc, Vol.1,No.3,(1954) ,pp.839.
[10] A. Maujean, and J.Chuche, Condensation of Iminines with acetyl chloride and Trimethyl amine, Tet.Lett.,Vol.1,No.1, (1976) ,pp. 2905-8.
[11]-Gunav,V.I;Mikhailopulo,I- A;Ovechkina ,L.F and Zavyalov, S. I; Chem. Abst., 1967,67,5497.
[12]- Ficini, J. and Genet, J.P; Soc. Chim. Fr., 1974, 2086.
[13]-Fietch,H.;Glauss,K.;Schmidt, E and  Jensen, H.; Chem.Abst.,1976,84,13568f.
[14]- Kato,T,;Ymamota,Y., Chem.Pharm.Bull. ,1967,15,1334.[15]- Kato,T .and Sakamoto, T.,Chem.Abst.,1968,68,11452.
[16]-Matsuda,I.,;Yamato,S.,and  Ishii,Y.; J.Chem.Soc . perkin Trans. (1)         ,1976,1933.
 [17]-Eckhardt, H.H and Perst,H. ;Tet.Lett .,1979,23 2125.
[18]- Obaid, H., A; National J. ,Chem. Vol. (7),446-460,(2002).
[19]-  W.F. Alhity;  ), Journal of Um-Salama for Science  Vol.      3,No. 1,  (2005), pp. 93-102.
  [20]- Hou, J. P., and Poole, J. W.: J. Pharm . Sci. 58:1150, 1969
 [21]- Waleed,F.Al-hiti and Mohammad,A.Al-Hadithi (Synthesis and characterization of Oxazepine, Oxazepane from reaction of (Schiff-bases) with maleic and Succinic anhydride., J.Of Al-Nahrain   university, 2005,8(2),27.
[22]- T.Tyoji, I. Kuniyoshi, and T. Takashi, Chem., Pharm. Bull., 1987,   35(8), 74.
[23]- F.A.Hussein, O.H.Abid (Synthesis of some Barbiturates via (Schiff  bases). Iraqi Journal of Chemistry ,2000,26,(1),216.
[24]- R.Huisgen,Chem.Internt.,1968,Edit.7,321.
[25]- M.M.Robert,and W.J.Charless,(Organic Chemistry AProblms; An Approach,) W.A. Bengamine, Inc,p526 (1975).