Facile stereoslective synthesis of spiro[indole-oxiranes] by combination of phase transfer catalyst and ultrasound irradiation and their bioassay.

作者: Anshu Dandia , Ruby Singh , Sumit Bhaskaran

DOI: 10.1016/J.ULTSONCH.2010.12.010

关键词:

摘要: Abstract An alternative and environmentally benign pathway for diastereoslective synthesis of fluorinated spiro[indole-3,2′-oxirane]-3′-benzoyl-2(1H)-ones (2a–g) is reported. The spiro[indole-3,2′-oxiranes] derivatives were obtained in 90–97% yield exclusively via the epoxidation 3-aroylmethylene indole-2-ones with 30% aqueous hydrogen peroxide using cetyltrimethyl ammonium bromide as a phase transfer catalyst under ultrasound irradiation. lead compounds have been tested their antimicrobial activity antioxidant properties.

参考文章(53)
C Dinesh Kumar, Annie Shirwaikar, K Rajendran, In vitro antioxidant studies of Annona squamosa Linn. leaves. Indian Journal of Experimental Biology. ,vol. 42, pp. 803- 807 ,(2004)
Milos Hudlicky, Attila E. Pavlath, Chemistry of organic fluorine compounds II : a critical review American Chemical Society. ,(1995)
Jean-Louis Luche, Synthetic Organic Sonochemistry ,(1998)
R. Kikumoto, T. Kobayashi, The reactions of oxindoles and isatin with nitrobenzyl chlorides Tetrahedron. ,vol. 22, pp. 3337- 3343 ,(1966) , 10.1016/S0040-4020(01)92520-7
Richard J. Sundberg, The chemistry of indoles ,(1970)
H. P. Sigg, H. P. Weber, Isolation and structure elucidation of ovalicin Helvetica Chimica Acta. ,vol. 51, pp. 1395- 1408 ,(1968) , 10.1002/HLCA.19680510624
YOSHIKAZU SATO, HIRO-OMI WATABE, TADASHI NAKAZAWA, TAKASHI SHOMURA, HARUO YAMAMOTO, MASAJI SEZAKI, SHINICHI KONDO, ANKINOMYCIN, A POTENT ANTITUMOR ANTIBIOTIC The Journal of Antibiotics. ,vol. 42, pp. 149- 152 ,(1989) , 10.7164/ANTIBIOTICS.42.149
Kapil Arya, Anshu Dandia, The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs. Bioorganic & Medicinal Chemistry Letters. ,vol. 18, pp. 114- 119 ,(2008) , 10.1016/J.BMCL.2007.11.002
Kaneyoshi Kato, Shinji Terao, Norio Shimamoto, Minoru Hirata, Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids Journal of Medicinal Chemistry. ,vol. 31, pp. 793- 798 ,(1988) , 10.1021/JM00399A019