• Title/Summary/Keyword: Isoxazolines

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An Efficient Synthesis of New Pyrazolines and Isoxazolines Bearing Thiazolyl and Etheral Pharmacophores

  • Bhosle, Manisha R.;Mali, Jyotirling R.;Pratap, Umesh R.;Mane, Ramrao A.
    • Bulletin of the Korean Chemical Society
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    • v.33 no.6
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    • pp.2012-2016
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    • 2012
  • A convenient synthetic route has been developed to synthesize 5-(4-((2-phenylthiazol-4-yl) methoxy)phenyl)-3-(4-sustituted phenyl)pyrazolines (5a-f) and 5-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-3-(4-substituted phenyl)isoxazolines (6a-f) starting from 2-phenyl-4-chloromethylthiazole (1). The chloromethylthiazole (1) was first condensed with 4-hydroxy benzaldehyde (2) for obtaining 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3). Claisen-Smidth condensation of 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3) and acetophenones has been carried in alkaline alcohol and obtained 3-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-1-(4-substituted phenyl)prop-2-en-1-ones (4a-f). The cyclocondensation of 2-propen-1-ones has been first time carried separately with hydrazine hydrate and hydroxylamine hydrochloride in aqueous micellar tetradecyltrimethylammonium bromide (TTAB) medium for getting the titled heterocycles with good to excellent yields.

Debromination of 3-(1,2-Dibromo-2-methylpropyl)-1,2-isoxazolines to 3-(2-Methyl-1-propenyl)-1,2-isoxazolines by Sodium Thiolates (3-(1,2-디브로모-2-메틸프로필)-1,2-이속사졸린들의 나트륨 티올레이트들에 의한 탈브롬화 반응을 통한 3-(2-메틸-1-프로페닐)-1,2-티올레이트들에 의한 탈브롬화 반응을 통한 3-(2-메틸-1-프로페닐)-1,2-이속사졸린들로의 변환반응)

  • Kim, Hyeong Cheol;Jo, Su Yeon;Jeon, Dong Ju;Kim, Hyeong Rae
    • Journal of the Korean Chemical Society
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    • v.45 no.6
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    • pp.608-611
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    • 2001
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Synthesis and Antimicrobial Activity of some New 2-Indolinone Derived Oximes and Spiro-Isoxazolines

  • El Gendy, Adel A.;Ahmedy, Aly M.
    • Archives of Pharmacal Research
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    • v.23 no.4
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    • pp.310-314
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    • 2000
  • The synthesis and spectral analysis of some new 1,3-dihydro-3-hydroxy-3-[2-hydroxyimino-2-(substituted phenyl)ethyll-2H-indol-2-ones (21-32) and spiro[3H-indol-3,5'-(4'H)-isoxazol]-2(1 H)-ones (33-44) are described. Sixteen of the synthesized compounds were screened in vitro for their growth inhibitory activity against thirteen species of microorganisms, viz, S. aureus, S. epidermidis, S. faecalis, B. subtilis, B. cereus, E. aerogens, E. coli, P. aeruginosa, P. vulgaris, A. baumonia, A. faecalis, C. albicans and S. cervicae. Most of the compounds exhibited significant antimicrobial activity especially the oximes 28 and 29.

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A Facile Greener Assisted Protocol for the Synthesis of Some New 4-aryl-(5-chloro-3-Methyl-1-phenyl-1H-Pyrazol-4-yl)-4,5-dihydroisoxazol-3-yl) Derivatives and their in vitro Antimicrobial Activity

  • Shaikh, Baseer M.;Konda, Shankaraiah G.;Yemul, Omprakash S.;Dawane, Bhaskar S.
    • Journal of the Korean Chemical Society
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    • v.56 no.2
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    • pp.246-250
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    • 2012
  • An efficient access, single step and environmentally benign synthesis of a new series of pyrazole containing isoxazolines derivatives were prepared by the condensation of chalcones bearing pyrazole moiety with hydroxyl amine hydrochloride in basic condition by using polyethylene glycol-400 (PEG) as a greener reaction solvent. The advantages of the present methodology are mild reaction condition and avoidance of volatile organic solvent. Furthermore, these newly synthesized compounds were screened for their antimicrobial activity against various pathogens like Escherichia coli (MTCC 2939), Salmonella typhi (MTCC 98), Staphylococcus aureus (MTCC 96), Bacillus subtilis (MTCC 441), Aspergillus niger (MTCC 281), Aspergillus flavus (MTCC 2501), Penicillium chrsogenum (MTCC 160) and Fusarium moniliformae (MTCC 156). Especially compound containing the hydroxyl group in C2-position and presence of halo (I, Br and Cl) groups as substituents at $C_3$ and $C_5$ position on the benzene nucleus showed the higher activity. Furthermore, compounds bearing methyl groups in combination with I and Br which enhanced the activity.