Synthesis of Some Heterocyclic Compounds Derived from 1-Aryl-3-( 4-hydroxy-3-methoxyphenyl ) propene-1-one

A series of heterocyclic compounds have been synthesized using 1–aryl-3-(4-hydroxy-3methoxypheny) prop-2-ene-1-one (1-4) as starting material which was prepared by claisenschmidt condensation between vanillin and substituted acetophenone.Benzoxazepine derivatives (5-8) and benzodiazepine derivatives (9-12) were synthesized from the reaction of o-aminophenol, o-phenlendiamine with compounds (1-4) respectively. Thereaction of compounds (1-4) with hydrazine hydrate afforded pyrazol derivatives (13-16). While the reaction of compounds (1-4) with hydrazine hydrates in the presences a few drops of glacial acetic acid gave 1acetyl pyazol derivatives (17-20). Oxirane derivatives (21-24) were synthesized from the reaction of compounds (1-4) with hydrogen peroxide in the basic medium. Reaction of phenylthiourea with compounds (1-4) afforded pyrimidinethion derivative (2527).Finally isoxazol derivatives (28-31) were synthesized by the reaction of compounds (1-4) with hydroxylamine hydrochloride in presences of triethylamine.


Introduction
The chemistry of chalcone characteristic by extensive scientific studies by a number researchers, some of these chalcone synthesis by the reaction of acetophenone with substituted aldehyde (1) othersreseacherersuse micro wave technology for preparation of a number of these derivatives (2) .This type or compounds encouraged us to synthesize a new heterocyclic derived from these compounds.etrocycliccompounds have dispelled an impressive array of biological activity among which anti-malarial (5) , anti-protozoa (6) , anti-Inflammatory (7) and immunlodulatory (8) .General procedure for synthesis of 1-aryl-3-(4-hydroxy-3-methoxyphenyl) prop-2-ene-1one (9) (1-4).

Synthesis of Some Heterocyclic Compounds
A mixture of (1.52g, 0.01mol) vanillin, (0.01mol) substituted acetophenone in 20ml absolute ethanol and 10 drops of thionyl chloride were stirring for 10 hr., and then refluxed for 6hr.The solvent was evapored under reduce pressure crush ice was added to the precipitate and left in cool condition overnight , the precipitate separated by filtration, dried and recrystallized from ethanol , The physical properties and spectral data were listed in Tables (1 , 9 ).
the excess of solvent was removed, and the product washed with water then recrystallized from ethanol.The physical properties and spectral data were listed in Tables (5, 13)
The reaction of chalcone derivative with o.phenylenediamine afforded benzodiazepine derivatives (9-12) which were identified by IR spectrum through the appearance of the following stretching bands; at (1609-1655 cm -1 ) for C=N group,( 3118-3287 cm -1 ) for N-H stretching, while (3275-3367 cm -1 ) for O-H stretching and absorption band within the range ( 1241-1277 cm -1 ) due to C-N stretching , The spectrum was also characterized by the absence of C=C and C=O groups.
Condensation of ofchalcone derivatives with hydrazine hydrate in glacial acetic acid as solvent afforded pyrazole derivatives (13-16) which were identified by IR.These spectra showed the absence of stretching banding of the carbonyl, C=C groups and the appearances of new bands at (1605-1695 cm -1 ) for C=N stretching vibration and bands absorbed at (3166-3332cm -1 ) and (3524-3584 cm -1 ) (21) for N-H and O-H respectively, also N-N stretching vibration was absorbed at (1020-1033 cm -1 ) as shown in Table ( 12) The condensation of compounds (1-4) with hydrazine hydrate in absolute ethanol in the presence of a few drops of glacial acetic acid afforded 1-acetylpyrazol derivatives (17-20)   which were identified by IR.The appearance of bands at (1506-1596 cm -1 ) for the C=N (22) stretching vibration.Bands at (1426-1507cm -1) for N-N stretching vibration band.The spectrum also showed band at (3612-3499cm -1 ) for O-H,also FT-IR indicated by the appearance of band at (1596-1646cm -1 ) for carbonyl group, as well as the disappearance of stretching bands related to C=C group, table (13).Shows the spectral data of these compounds.

Synthesis of Some Heterocyclic Compounds
Compounds (21-24) were identified by the appearance of the following bands; at (1640-1653 cm -1 ) for carbonyl group , bands at (1076-1168cm -1 )& (1278-1285cm -1 ) for symmetrical and asymmetrical (C-O-C) bonds stretching respectively and the band absorbed within the range (3177-3669 cm -1 ) due to the O-H stretching , also the spectrum characterized by the absent of band for C=C group.Table (14) shows some spectral data of these compounds.
The IR spectra for isoxazole compounds (28-31) shows absorption bands at (1614-1654 cm -1) attributed to the stretching vibration of C=N.The spectra were also showed absorption bands at (1106-1091cm -1 ) & (1265-1272cm -1 )for symmetrical and asymmetrical C-O-C bonds stretching, while the bands at ( 750-784 cm -1 ) attributed to the N-O bonds.Also the spectrum shows the absent of C=C group.Table (16) shows some spectral data of these compounds.

Synthesis of Some Heterocyclic Compounds
In this paper chalcone derivatives was used as important starting materials for the synthesis of various classes of heterocyclic compounds such as isoxazole, pyrazolines, substituted pyrazolines and pyrimidinone derivative.Many1, 5-benzoxazepines and benzodiazepine derivative were also prepared.ExperimentalMelting points were measured on Electro thermal Melting Point Apparatus and are uncorrected.The IR spectra were recorded by using infrared spectrophotometer model Tensor 27 Bruckner Co. Germany.Ultra violet light recorded by Shimadzu UV-210 Double-Beam Spectrophotometer in DMF as solvent.