Synthesis of some Heterocyclic Compounds from 1 , 4-Benzoxazine-3-one

The compound (1) was synthesized by reacting 2-amino phenol with ethyl bromo acetate.The treatment of ethyl bromo acetate with compound (1) gave (2), While compound (3) was produced by reacting hydrazine hydrate with compound (2). Compound (3) was used as precursor to prepare (4-12) by reacting it with different chemical reagents. The reaction of (11) with thioglycolic acid, 3-chloro perbenzoic acid afforded (13,14) respectively, while compound (15) was prepared from the reaction of (12) with chloro acetyl chloride. The products were identified by physical, chemical and spectroscopic methods. Introduction Derivatives of 2,3-dihydro-3-oxo-1,4-benzoxazine are well known. these nitrogen-oxygen containing heterocyclic compounds were prepared by heating α-halogenacyl-o-anisidides with aluminum chloride as catalyst. Versatile methods were used for the preparation of these compounds using o-amino phenoxy acetic acid in presence of platinum oxide or o-chloro acetamido phenol in weakly alkaline solution. Synthesis of some Heterocyclic Compounds from 1,4-Benzoxazine-3-one. 2 Various benzoxazine derivatives have been shown to have interesting pharmacological properties. A group of 1,4-benzoxazine-3-one was isolated from maize, wheat and rye, therefore 2H-1,4-benzoxazine -3(4H)one was used as heterocyclic scaffolds for design of cardiovascular, anti psychotic, anti depressive and anti bacterial drugs, like 2,4dihydroxy-(2H)-1,4-benzoxazine-3-(4H) one


Introduction
Derivatives of 2,3-dihydro-3-oxo-1,4-benzoxazine are well known (1) .these nitrogen-oxygen containing heterocyclic compounds were prepared by heating α-halogenacyl-o-anisidides with aluminum chloride as catalyst (2) .Versatile methods were used for the preparation of these compounds using o-amino phenoxy acetic acid in presence of platinum oxide or o-chloro acetamido phenol in weakly alkaline solution (1,3) .Various benzoxazine derivatives have been shown to have interesting pharmacological properties (4) .A group of 1,4-benzoxazine-3-one was isolated from maize, wheat and rye (5) , therefore 2H-1,4-benzoxazine -3-(4H)one was used as heterocyclic scaffolds for design of cardiovascular, anti psychotic, anti depressive and anti bacterial drugs (6,7)  Interesting bioactivity was observed for both compounds, some of their degraded products, and also some synthetic analogues shows antimicrobial, antifeedant, insecticidal (8) , and were found to inhibit germination of spores of the phytopathogenic fung (5) .N-alkylation of 2H-1,4-benzoxazine-3-one was performed to prepare N-ester, and hydrazide compounds by treatment with ethyl bromo acetate in presence of anhydrous potassium carbonate (9) , The above compound was also used to prepare hydrazide compound by the treatment of this compound with hydrazine hydrate (10) .Preparation of Some heterocyclic compounds by the treatment of hydrazide derivative with different chemical reagent.As mentioned heterocyclic compounds were prepared from hydrazide derivatives may be beneficial as bioactivities.

Experimental
1. Melting points were determined by Electro thermal IA 9000.2. Infra red spectrophotometer Model Tanser 27 Bruker Co. Germany was used to measure the IR spectra.

Results and discussion
The parent compound (1) was prepared by reaction of ethyl bromo acetate with 2-amino phenol in presence of sodium ethoxide.The ester compound (2) was prepared by reacting of compound (1) with ethyl bromo acetate in presence of potassium carbonate.The ester compound (2) was identified by the appearance of the following band at (1739 cm -1 ) for the ester carbonyl band, carbonyl of amide at (1680 cm -1 ) and disappearance of N-H stretching for amide, (2914 cm -1 ) for C-H stretching and (1280 cm -1 ,1090 cm -1) for C-N band and appear C-H band for CH 3 at (1377 cm -1 ).The ester compound (2) was reacted with excess amount of hydrazine hydrate to produce hydrazide compound (3), the hydrazide compound was identified by disappearance of ester carbonyl band and the appearance of the following bands (1688 cm -1 , 1671 cm -1 ) for amide carbonyl of lactone & hydrazide respectively, (1284 cm -1 ) for C-N, C-H band was shown at (2852 cm -1 ) and another band at (3334 cm -1 ) for N-H stretching.compound (3) was used to prepare a number of heterocyclic compounds as indicated in scheme (1).The compounds (4-6) were synthesized by the reaction of hydrazide (3) with carbon disulphide in ethanolic solvent, α-chloro acetamide in presence of triethylamine or α-chloro acetic acid in presence of sodium acetate and acetic acid to produce compounds 4,5,6 respectively.
The IR spectra of compound (13) showed significant absorption bands at 1738 cm -1 which due to stretching vibration of amide carbonyl while the band at 3446 cm -1 for N-H while C-H band appeared at 2923 cm -1 and C-S band appeared at 747 cm -1 .
Compound (14) was synthesized by the reaction of compound (11) with oxidizing reagent 3-chloro per benzoic acid to give compound (14).
The structure of compound (14) was identified by the following significant absorption bands at 3214 cm -1 for N-H stretching, amide carbonyl at 1674 cm -1 and C-O at 1055 cm -1 and N-O band at 816 cm -1 , C-H band at 2900 cm -1.Compound (15) was synthesized by the reaction of compound (12)  with chloro acetyl chloride to give compound (15).
The structure of this compound was identified by IR spectroscopic data shown in the significant absorption peak at 3187 cm -1 due to N-H stretching and the carbonyl of the new ring appeared at 1739 cm -1 , carbonyl of the amide appeared at 1699 cm -1 , while N=O band sym, asy absorbed at 1353 cm -1 , 1531 cm -1 respectively, C-H band at 2948 cm -1 and C-Cl band at 699 cm -1 .