J.

Atoms and Molecules / 2(5); 2012 / 356360 Research Article

Tejas Vyas et al

Journal of Atoms and Molecules

An International Online Journal
ISSN 2277 1247

SYNTHESIS AND CHARACTERIZATION OF VARIOUS 3-[3,5-BIS (TRIFLUOROMETHYL)PHENYL]-5-(SUBSTITUTED PHENYL)-1,2-ISOXAZOLE Tejas Vyas1*, Kiran Nimavat2, Kartik Vyas3
1

Research Scholar JJT University, Rajasthan, India 2 Govt. Science College, Gandhinagar 3 Sheth L.H. Science College, Mansa Revised on: 08-10-2012 Accepted on: 18102012

Received on: 28-09-2012 Abstract:

Some novel heterocyclic compounds containing isoxazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods Key Words: Isooxazole; 3-[3,5-bis(trifluoromethyl)phenyl]-5-(Substituted phenyl)-1,2-isoxazole; Hydroxyl amine hydrochloride, isooxazole compounds

Introduction: Chalcones are synthesized by condensing ketones with aromatic aldehydes in the * Corresponding author Tejas Vyas, Email: tv71104@yahoo.com Tel: +91 9879104795 presence of suitable bases. They are very useful intermediates for the synthesis of five[1,2], sixheterocyclic
[5-14] [1,3] [4]

and seven-membered compounds.

Chalcone

derivatives exhibit diverse pharmacological activities . It is therefore, not surprising

that many synthetic methods have been developed for the preparation of heterocycles starting from chalcone precursors that have been tested for their antimicrobial activities. All rights reserved 2011 www.jamonline.in 356

J. Atoms and Molecules / 2(5); 2012 / 356360 Earlier we have reported Synthesis of novel 4[3,5-bis(trifluoromethyl)phenyl]-6 (Substituted phenyl)-1,6-dihydropyrimidine2-thiol[15]. Synthesis and Characterization of novel 6[3,5-bis(trifluoromethyl)phenyl]-4(substitutedphenyl)-1,4-dihydropyrimidin-2ol[16]. Synthesis, characterization and biological screening of novel (E)-1(3,5-

Tejas Vyas et al TMS as internal standard and chemical shifts are indicated in (ppm). The progress of the reaction was monitored on precoated silica gel 60 F 254 plates (Merck) using different solvent systems and visualizing the spots under ultraviolet light and iodine chamber. Elemental analyses for C, H and N were carried out using a Perkin -Elmer C, H, and N analyzer. Method for Synthesis of novel 3-[3,5bis(trifluoromethyl)phenyl]-5-(Substituted phenyl)-1,2-isoxazole: A mixture of (2E)-1[3,5-bis(trifluoromethyl)phenyl]-3-(2-

bis(trifluoromethyl)phenyl)-3(substituted)phenylprop-2-en-1-one[17]. In the present communication we wish to report the reaction of various with novel

methoxyphenyl)prop-2-en-1-one, (0.02 mol), hydroxylamine hydrochloride(0.02 mol) and sodium acetate in ethanol (25 ml) was refluxed for 6hr. The mixture was

halosubstituted

chalcones

hydroxyl

amine hydrochloride. The structures of the various synthesized compounds were assigned on the basis of IR, 1H-NMR spectral data and elemental analysis. These compounds were also screened for their antimicrobial activity. Materials and methods: The solvents and reagents used in the synthetic work were of analytical grade obtained from Hi-media and were purified by distillation or crystallization where necessary and their boiling or melting points were compared with the available literature values. Melting points were determined in open capillaries and are uncorrected. IR spectra were recorded FTIR Unicorn Maltson 1000 spectrophotometer.1H-NMR recorded on Bruker spectra (80 were MHz)

concentrated by distilling out the solvent under reduced pressure and poured into ice water. The precipitate obtained was filtered, washed and recrystallized. The completion of the reaction was monitored by TLC. All the above compounds were purified by means of silica gel column and confirmed by 1H NMR and 13C NMR, IR, Mass and Elemental analysis. (2a). 3-[3,5-bis(trifluoromethyl)phenyl]-5-

(2-Methoxy phenyl)-1,2-isoxazole MS; m/z 387; mp 278oC; Anal. Calcd. For C18H11F6NO2; C, 55.82; H, 2.86; F, 29.43; N, 3.62; O, 8.26; Found; C, 55.76; H, 2.73; F, 29.39; N, 3.57; O, 8.22; IR (cm-1): 3049 (C-H stretching of aromatic ring), 1703 (C=O www.jamonline.in 357

Ac-80

spectrometer (300MHz in DMSO-d6 ) using All rights reserved 2011

J. Atoms and Molecules / 2(5); 2012 / 356360 stretching ), 1681, 1585 and 1531 (C=C stretching of aromatic ring), 1240 (N-O stretching ), 1084 (C-H in plane deformation of aromatic ring), 1012 (C-F stretching), 829 (C-H out of plane bending of 1,4(2e).

Tejas Vyas et al 3-[3,5-bis(trifluoromethyl)phenyl]-5-

(3-Chloro phenyl)-isoxazole MS; m/z 391; Anal. Calcd. For

C17H8ClF6NO; C, 52.13; H, 2.06; Cl, 9.05; F, 29.10; N, 3.58; O, 4.08; Found; C, 52.02; H, 2.02; Cl, 9.01; F, 29.04; N, 3.49; O, 4.01. (2f). 3-[3,5-bis(trifluoromethyl)phenyl]-5-

disubutituion); 1H NMR (DMSO-d6) ppm: 6.7 to 6.9 (m, 4H aromatic), 3.86 (s, 3H, OCH3), 7.52-7.58 (m, 3H aromatic

fluorinated ring). Similarly remaining compounds were

(3-Methoxy phenyl)-isoxazole MS; m/z 387; Anal. Calcd. For C18H11F6NO2; C, 55.86; H, 2.86; Cl, 29.43; N, 3.62; O, 8.26; Found; C, 55.76; H, 2.72; F, 29.32; N, 3.54; O, 8.12.

confirmed by element analysis and their mass spectra. (2b). 3-[3,5-bis(trifluoromethyl)phenyl]-5-

(2-Chloro phenyl)-isoxazole MS; m/z 391; Anal. Calcd. For

(2g).

3-[3,5-bis(trifluoromethyl)phenyl]-5-

(3,4 Dimethoxy phenyl)-isoxazole C17H8ClF6NO; C, 52.13; H, 2.06; Cl, 9.05; F, 29.10; N, 3.58; O, 4.08; Found; C, 52.08; H, 2.04; Cl, 9.01; F, 29.01; N, 3.43; O, 4.01. (2c). 3-[3,5-bis(trifluoromethyl)phenyl]-5(2h). 3-[3,5-bis(trifluoromethyl)phenyl]-5(3,4-Dichloro phenyl)-isoxazole MS; m/z 375; Anal. Calcd. For C17H8F7NO; C, 54.41; H, 2.15; F, 35.44; N, 3.73; O, 4.26; Found; C, 54.31; H, 2.06; F, 35.37; N, 3.63; O, 4.15. (2d). 3-[3,5-bis(trifluoromethyl)phenyl]-5(2i). Calcd. For MS; m/z 391; Anal. Calcd. For C17H8ClF6NO; C, 52.13; H, 2.06; Cl, 9.05; F, 29.10; N, 3.58; O, 4.08; Found; C, 52.02; H, 2.02; Cl, 9.01; F, 29.04; N, 3.49; O, 4.01. 3-[3,5-bis(trifluoromethyl)phenyl]-5(4-Chloro phenyl)-isoxazole MS; m/z 436; Anal. C17H8BrF6NO; C, 46.82; H, 1.85; Br, 18.32; F, 26.14; N, 3.21; O, 3.67; Found; C, 46.71; H, 1.67; Br, 18.21; F, 26.05; N, 3.11; O, 3.54. MS; m/z 426; Anal. Calcd. For C17H7Cl2F6NO; C, 47.91; H, 1.66; Cl, 16.64; F, 26.75; N, 3.29; O, 3.75; Found; C, 47.84; H, 1.53; Cl, 16.53; F, 26.64; N, 3.15; O, 3.65. (2-Bromo phenyl)-isoxazole MS; m/z 417; Anal. Calcd. For C19H13F6NO3; C, 54.69; H, 3.14; F, 27.32; N, 3.36; O, 11.50; Found; C, 54.52; H, 3.07; F, 27.23; N, 3.24; O, 11.43. (2-Fluoro phenyl)-isoxazole

All rights reserved 2011

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J. Atoms and Molecules / 2(5); 2012 / 356360 (2j). 3-[3,5-bis(trifluoromethyl)phenyl]-5(2l).

Tejas Vyas et al 3-[3,5-bis(trifluoromethyl)phenyl]-5-

(4-Fluoro phenyl)-isoxazole MS; m/z 375; Anal. Calcd. For C17H8F7NO; C, 54.41; H, 2.15; F, 35.44; N, 3.73; O, 4.26; Found; C, 54.31; H, 2.06; F, 35.37; N, 3.63; O, 4.15. (2k). 3-[3,5-bis(trifluoromethyl)phenyl]-5-

(2,4-Dimethyl phenyl)-isoxazole MS; m/z 385; Anal. Calcd. For C19H13F6NO; C, 59.23; H, 3.40; F, 29.58; N, 3.64; O, 4.15; Found; C, 59.15; H, 3.32; F, 29.43; N, 3.52; O, 4.05. All the above compounds were purified by means of silica gel column and confirmed by Calcd. For 1H NMR, IR, Mass and Elemental analysis. Antimicrobial study of the above synthesised compound was also carried out.

(4-Bromo phenyl)-isoxazole MS; m/z 434; Anal.

C17H8BrF6NO; C, 46.82; H, 1.85; Br, 18.32; F, 26.14; N, 3.21; O, 3.67; Found; C, 46.71; H, 1.67; Br, 18.21; F, 26.05; N, 3.11; O, 3.54.

CF3

NH2OH.HCl/ CH3COONa Methanol CF3

CF3 R N O

CF3 O

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