Synthesis of 3-Phenyl-4 [ 4-( m-nitrophenyl )-N-2-( 2 ’-arylureido / arylthioureido-4 ’N-morpholino-s-triazin )-benzo-[ 6 , 7 ]-coumarins and their Applicatiions

Several 3 – phenyl – 4 [4-(m – nitrophenyl) – N – 2 (2’-arylureido /arylthioureido 4’N -morpholino-s-triazin)-benzo-(6,7)-coumarins were prepared using 2-(m–nitrophenyl)-3-hydroxy naphthalene, cyanuric chloride, morpholine and various aryl – ureas / aryl – thioureas derivatives to give desired compound. The structures of the compounds were confirmed by elemental analysis and spectral analysis. The antibacterial activities of these compounds have been screened and were also applied as Flourescent Brighteners on Polyester fabrics.

Also coumarins have played and important role in textile chemistry and subsequently emerged as fluopore [12][13][14][15] .The coumarin ring system substituted by (hetero) aromatic residues or electro-attracting substituents are characterized by their high light stability.The present study reports the synthesis, application, absorption, characteristics and fastness properties and important biological activities displayed by triazinyl amino coumarin derivatives having following structure.

Arylureas and arylthioureas
The starting compounds arylureas 17 and arylthioureas 18 are prepared by the known methods.

2-Phenyl-2-(m-nitrophenyl)-3-naphthylacetate
A mixture of 2-(m-nitroanilide)-3-hydroxynaphthalene (0.01 mol) and phenylaceticacid (0.01mol) was stirred with pyridine (20 mL) for an hour to get a clear solution.Phosphorous oxychloride (2.5 mL) was then added in about 15 min.at such a rate that the temperature of the mixture did not rise above 50°C.the mixture was stirred for an hour and diluted with hydrochloric acid.The solid obtained was filtered, washed first with water, then with sodium bicarbonate solution (10% W/V) and again with water, dried and crystallized from acetone to get light pink crystals, yield 84%, m.p.142°C.
To this slurry a solution of 3-phenyl-4-(m-nitroanilide)-benzo-[6,7-b]-coumarin (0.01 mol) in acetone (20 mL) was then added at such a rate that the temperature of the mixture did not rise above 4C.the mixture was stirred for 3-4 hours at 0-5°C, maintaining pH 7.0 by the addition of sodium -carbonate solution (10% W/V)(if necessary).The product was filtered, washed with cold -water, dried and crystallized from benzene to get pale yellow crystals, yield 67%,m.p.125°C.

Biological Screening
All the compounds were screened for antibacterial activity following disc-agar diffusion method at a concentration of 15 mcg/disc against S.aureus, S.pyogenes (gram-negative bacterial strain) and E.coli and K.pneumoniae (gram -positive bacterial strain).The test organisms were maintained on nutrient agar glant.Nutrient broth was used as the medium for testing.The compounds were vinitially dissolved in 25 % DMF and then dispended in different volumes of sterile nutrients broth contained in tubes.After the compound was mixed, the medium was inoculated with twenty-four old-culture of the test organism.The tubes were then incubated at 37°C up to forty-eight hours and results are summarized in Table 1.
The analytical and characterization data's are represented in Table 1.

Dyeing
These compounds were applied to polyester fabrics as fluorescent brighteners using reported procedure 16 and Fastness tests were assessed by the standard methods of testing (BS :1006 -1978 and IS : 765 -1979).
ExperimentalAll the melting points are taken in open capillaries and are uncorrected.Absorption and fluorescence emission spectra were recorded on a Hitach U -320 spectrometer and Jobin Yvon JY 3CS spectrophotofluorometer respectively.,IR spectra were recorded on Perkin Elmer 377 -spectrometer, while 1 H NMR spectra on a Varian 60 MHz instrument EM -360 -L using TMS as internal standard and CDCl 3 + DMSO -d 6 as solvent.Elemental analysis was performed on Carlo -Erba 1108 analyzer.

Table 1 .
Analytical and antimicrobial activity data of the compounds 1 -26.

Table 2 .
Absorption -Emission and Fastness Evaluation Data of the compounds 1 -26.