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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 14
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Original Articles

Synthesis of New Spiro[1,4,2-dioxazole-5,3′-indolin]-2′-one by 1,3-Dipolar Cycloaddition

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Pages 2096-2102 | Received 18 Feb 2010, Published online: 20 May 2011

REFERENCES

  • James , M. N. G. ; Williams , G. J. B. The molecular and crystal structure of an oxindole alkaloid (6-hydroxy-2′-(2-methylpropyl)-3,3′-spirotetrahydropyrroIidino-oxindole) . Can. J. Chem. 1972 , 50 , 2407 – 2412 .
  • Elderfield , R. C. ; Gilman , R. E. Alstonia alkaloids, 11: Alkaloids of alstonia muelleriana . Phytochemistry 1972 , 11 , 339 – 343 .
  • Jossang , A. ; Jossang , P. ; Hadi , H. A. ; Sevenet , T. ; Bodo , B. Horsfiline, an oxindole alkaloid from Horsfieldia superba . J. Org. Chem. 1991 , 56 , 6527 – 6530 .
  • Cui , C. B. ; Kakeya , H. ; Okada , G. ; Onose , R. ; Osada , H. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus, 1: Taxonomy, fermentation, isolation and biological properties . J. Antibiot. 1996 , 49 , 527 – 533 .
  • Jain , M. ; Khanna , P. ; Saxena , A. ; Bhagat , S. ; Olsen , C. E. ; Jain , S. C. Synthesis of some novel bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4′-diones . Synth. Commun. 2006 , 36 , 1863 – 1872 .
  • Piscopo , E. ; Diurno , M. V. ; Mazzoni , O. ; Ciaccio , A. M. Studies on heterocyclic compounds spiroindole-3,2′-thiazolidine derivatives antimicrobial activity of monohalogenated 3′-phenylspiro-3H-indole-3,2′-thiazolidine-2,4′-1H-diones . Bull. Soc. Ital. Biol. Sper. 1990 , 66 , 1181 – 1186 .
  • Rajopadhye , M. ; Popp , F. D. Synthesis and antileukemic activity of spiro[indoline-3,2′-thiazolidine]-2,4′diones . J. Heterocycl. Chem. 1987 , 24 , 1637 – 1641 .
  • Kornet , M. J. ; Thio , A. P. Oxindole-3-spiropyrrolidines and -piperidines: Synthesis and local anesthetic activity . J. Med. Chem. 1976 , 19 , 892 – 898 .
  • Hershenson , E. M. ; Prodan , K. A. ; Kochman , R. L. ; Bloss , J. L. ; Mackerer , C. R. Synthesis of β-spiropyrrolidinoindolines, their binding to glycine receptor, and in vivo biological activity . J. Med. Chem. 1977 , 22 , 1448 – 1451 .
  • Jain , R. ; Bansal , M. A facile synthesis and central nervous system activities of fluorine containing spiro-[3H-indole-3,4′(4H)-pyran]-2(1H)-ones . Pharmazie 1995 , 50 , 224 – 225 .
  • Kikugawa , K. ; Ichino , M. Platelet-aggregation inhibitors, 5: Pyrimidine derivatives, indole derivatives, benzothiophenes, and benzoquinolizine derivatives . Chem. Pharm. Bull. 1973 , 21 , 1151 – 1155 .
  • Joshi , K. J. ; Jain , R. ; Chand , P. Indoles with C-3 as spiro atom . Heterocycles 1985 , 23 , 957 – 996 .
  • Flann , C. J. ; Overman , L. E. ; Sarkar , A. K. Synthesis of 3-acyl-3-alkyloxindoles . Tetrahedron Lett. 1991 , 32 , 6993 – 6996 .
  • Bouhfid , R. ; Joly , N. ; Ohmani , F. ; Essassi , E. M. ; Lequart , V. ; Banoub , J. ; Kheddid , K. ; Charof , R. ; Massoui , M. ; Martin , P. Synthesis and antibacterial activity of new (2,3-dioxo-indolin-1-yl) acetamides . Lett. Org. Chem. 2008 , 5 , 3 – 7 .
  • Bouhfid , R. ; Joly , N. ; Massoui , M. ; Cecchelli , R. ; Lequart , V. ; Martin , P. ; Essassi , E. M. An efficient synthesis of new spiro[indolo-3(1H),2′(3′H)-oxadiazolyl] and 1-(triazol-4-ylmethyl)isatin derivatives . Heterocycles 2005 , 65 , 2949 – 2955 .
  • Nyerges , M. ; Gajdics , L. ; Szollosy , A. ; Toke , L. 2-Oxoindolin-3-ylidene derivatives as 2 pi components in 1,3-dipolar cycloadditions of azomethine ylides . Synlett 1999 , 1 , 111 – 113 .
  • Malinakova , H. C. ; Liebeskind , L. S. Enantiocontrolled synthesis of spirooxindoles based on the [5 + 2] cycloaddition of a Tp(CO)(2)Mo(pyridinyl) scaffold (Tp = hydridotrispyrazolylborate) . Org. Lett. 2000 , 2 , 4083 – 4086 .
  • Cecchelli , R. ; Dehouck , B. ; Descamps , L. ; Fenart , L. ; Buée-Scherrer , V. ; Duhem , C. ; Rentfel , M. ; Torpier , G. ; Dehouck , M. P. In vitro model for evaluating drug transport across the blood–brain barrier . Adv. Drug Delivery Rev. 1999 , 36 , 165 – 178 .

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