Synthesis of new N-Substituted -3- chloro -2- azetidinones for 2, 4-Diamino-6-phenyl-1,3,5-triazine

: The current study involved synthesis of several new N-Substituted - 3-chloro -2- azetidinones for 2,4-Diamino-6-phenyl-1,3,5-triazine by two steps. The first step includes preparation of Schiff bases (A1-A6) by condensation of 2,4-Diamino-6-phenyl-1,3,5-triazine with many substituted aldehydes, then the second step includes preparation new six azetidinone compounds (B1-B6) by reaction of chloro acetyl chloride with the prepared Schiff bases in first step. The prepared compounds were characterized by physical properties, FT-IR, UV and some of them by 1 H-NMR, 13 C-NMR spectroscopy were recorded


Introduction:
Schiff bases are characterized by the (N=CH) imines group which important compounds in medicinal and pharmaceutical field [1].They show biological activities including antibacterial, antifungal [2,3] , anticancer [4] and herbicidal activities [5] figure (1) shows the stricture for this component.Fur their more Schiff bases have been widely used as protective group of amino group in organic synthesis [6,7] .Schiff bases react with chloroacetyl chloride to give (β -Lactam) 3-chloro-2azetidinones.

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The β -Lactam hetro cycles are still the most prescribed antibiotics used in medicine.They are considered as an important contribution of science to humanity [8] .The most widely used antibiotics such as the Penicillins, Cephosporins, Carumonam, aztreonam and Nocardincins all contain β -Lactam rings [9] .The long term use of β -Lactam antibiotics exerts selective pressure on bacteria and permits the proliferation of resistant organisms [10] .A comparative study of current antibiotics with those from decades shows an alarming increase in bacterial resistance to β -Lactam antibiotics [11] .The development of several synthetic and semisynthetic β -Lactam antibiotic by the pharmaceutical industry was due to the growing resistance of bacteria towards the β -Lactam antibiotics and the need for medicines with a more specific antibacterial activity.An interesting group of β -Lactam are the monocyclic β -Lactams, which are molecules that do not contain another ring fused to the β -Lactam one.Azetidinones, which are part of the antibiotic structure , are known to exhibit interesting biological activities [12] .Alarge number of 3-chloro mono cyclic β -Lactams possess powerful antibacterial, antimicrobial, antiinflammatory, anticonvulsant and ant tubercular activity [13] .

Material and Methods:
General: Chemicals employed were of analytical grade and used without further purification.Melting points were determined on Gallen kamp capillary melting point apparatus and were uncorrected.FT-IR spectra were recorded using KBr discs on SHIMADZU FT-IR 8400 Fourier Trans form Infrared spectrophotomet.U.V. spectra recorded using SHIMADZU UV-visible recording spectrophotometer U.V 160. 1 H-NMR and 13 C-NMR spectra were recorded on Brukerspecrosp in Ultra shield 300 MHZ in strumentusing tetramethylsilane (TMS) as an internal standard and DMSO-d6 as a solvent in Al-Albate University in Jordan.

fig.(4)
The reaction was followed by disappearance of (NH 2 ) absorption band at (3410-3298) cm -1 and appearance of (C=N) absorption band in the IR spectra of the products.(N-substituted-3-chloro-2-azetidinones) were prepared by reaction of chloro acetyl chloride with the prepared Schiff bases (A1-A6) in first step.The prepared compounds were characterized by physical properties, FT-IR, UV and some of them by 1 H-NMR , 13 C-NMR spectroscopy were recorded.

R=
The synthesis of these compounds was carried out lined in scheme 1.And the physical properties for compounds (B1-B6) including melting point range of ( 102-239) ºC and %yield were ranged (57.5-70) and these compounds were identified by FT-IR, UV, 1 H-NMR and 13 C-NMR spectroscopy.
FT-IR spectrum of compounds (B1, B5) showed clear absorption bands at (1735, 1705) cm -1 respectively at tribute to (C=O) imide stretching frequency is good evidence for the success of this step of reaction while disappearance of υ (C=N) absorption bands at (1670, 1662 )cm -1 respectivly in IR spectra of the products.The IR absorption bands are given in table ( 3) see fig.