Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 4
151
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Regioselective Synthesis of Dispirocycloalkanooxindolopyrrolidines and Dispirocyclalkanoindanopyrrolidines

, &
Pages 551-563 | Received 22 Feb 2009, Published online: 03 Feb 2010

REFERENCES

  • Padwa , A. 1,3-Dipolar Cycloaddition Chemistry , vols. 1 and 2 ; Wiley : New York , 1984 .
  • (a) Garner , P. ; Ho , W. B. ; Grandhee , S. K. ; Youngs , W. J. ; Kennedy , V. O. Development of an asymmetric approach to the 3,8-diazabicyclo[3.2.1]octane moiety of quinocarcin via intramolecular 1,3-dipolar cycloadditions of photochemically generated azomethine ylides . J. Org. Chem. 1991 , 56 , 5893 ; (b) Garner , P. ; Ho , W. B. ; Shin , C. The asymmetric synthesis of (−)-quinocarcin via a 1,3-dipolar cycloadditive strategy . J. Am. Chem. Soc. 1993 , 115 , 10742 – 10753 .
  • Monn , J. A. ; Valli , M. J. A concise, stereocontrolled thiazolium ylide approach to kainic acid. J. Org. Chem. 1994, 59, 2773.
  • Pham , V. C. ; Charlton , J. L. Methyl (S)-lactate as a chiral auxiliary in the asymmetric synthesis of Bao Gong Teng A . J. Org. Chem. 1995 , 60 , 8051 – 8055 .
  • Fiswick , C. W. G. ; Foster , R. J. ; Carr , R. E. A short dipolar cycloaddition approach to γ-lactam alkaloids from Cynometra henkei . Tetrahedron Lett. 1996 , 37 , 3915 – 3918 .
  • Baldwin , J. E. ; Mackenzie Turner , S. C. ; Malony , M. G. The synthesis of substituted pyrrolidines by a samarium(II) iodide–mediated ring closure, Part 1 . Tetrahedron 1994 , 35 , 9411 – 9424 .
  • Galeazzi , R. ; Geremia , S. ; Mobbili , G. ; Orena , M. Stereoselective reduction of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones . Tetrahedron:Asymmetry 1999 , 10 , 587 – 605 .
  • Obniska , J. ; Zeic , A. ; Zagorska , A. Synthesis and anticonvulsant properties of new 1-phenyl and 1-phenylamino-3-phenylpyrrolidine-2,5-dione derivatives . Acta Pol. Pharm. 2002 , 59 , 209 – 213 .
  • Padwa , A. Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon : Oxford , 1991 ; vol. 4 , p. 1085 .
  • Stylianakis , I. ; Kolocouris , A. ; Kolocouris , N. ; Fytas , G. ; Foscolos , G. B. ; Padalko , E. ; Neyts , J. ; De Clercq , E. Spiro[pyrrolidine-2,2′-adamantanes]: Synthesis, anti-influenza virus activity, and conformational properties . Bioorg. Med. Chem. Lett. 2003 , 13 , 1699 – 1703 .
  • (a) Carroll , W. A. ; Grieco , P. A. Biomimetic total synthesis of pseudotabersonine: A novel oxindole-based approach to construction of Aspidosperma alkaloids . J. Am. Chem. Soc. 1993 , 115 , 1164 – 1165 ; (b) Earley , W. G. ; Oh , T. ; Overman , L. E. Synthesis studies directed toward gelsemine: Preparation of an advanced pentacyclic intermediate . Tetrahedron Lett. 1988 , 29 , 3785 – 3788 .
  • Hilton , S. T. ; Ho , T. C. ; Pljevaljcic , G. ; Jones , K. A new route to spirooxindoles . Org.Lett. 2000 , 2 , 2639 .
  • Hall , H. I. ; Carlson , G. L. ; Abernethy , G. S. ; Piantadosi , C. Cycloalkanones, 4: Antifertility activity . J. Med. Chem. 1974 , 17 , 1253 – 1257 .
  • Ali , M. I. ; El-Kaschef , M. A.-F. ; Hammam , A. G. ; Khallaf , S. A. Reactions with (arylmethylene)cycloalkanones, 2: Synthesis of 10-(arylmethylene) hexahydrocyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin-3-one derivatives of probable anticancer activity . J. Chem. Eng. Data 1979 , 24 , 377 – 378 .
  • (a) Amal Raj , A. ; Raghunathan , R. A novel entry into a new class of spiroheterocyclic framework: Regioselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines and dispiro[oxindole-hexahydroindazole]pyrrolidines . Tetrahedron 2001 , 57 , 10293 – 10298 ; (b) Amal Raj , A. ; Raghunathan , R. ; Sridevikumari , M. R. ; Raman , N. Synthesis, antimicrobial, and antifungal activity of a new class of spiro pyrrolidines . Bioorg. Med. Chem. 2003 , 11 , 407 – 419 ; (c) Poornachandran , M. ; Raghunathan , R. Synthesis of dispirooxindolecycloalka[d]pyrimidino[2,3-b]-thiazole pyrrolidine/thiapyrrolizidine ring systems . Tetrahedron 2006 , 62 , 11274 – 11281 .
  • (a) Grigg , R. ; Surendrakumar , S. ; Thianpatanagul , S. ; Vipond , D. X˭Y-ZH systems as potential 1,3-dipoles, part 11: Stereochemistry of 1,3-dipoles generated by the decarboxylative route to azomethine ylides . J. Chem. Soc., Perkin Trans. 1 1988 , 2693 – 2702 ; (b) Grigg , R. ; Idle , J. ; McMeekin , P. ; Vipond , D. X˭Y-ZH systems as potential 1,3-dipoles, part 12: Mechanism of formation of azomethine ylides via the decarboxylative route from α-amino acids . J. Chem. Soc., Perkin Trans. 1 1988 , 2703 – 2714 ; (c) Tsuge , O. ; Kanemasa , S. Recent advances in azomethine ylide chemistry . Adv. Heterocycl. Chem. 1989 , 45 , 231 – 349 .
  • Baltzly , R. ; Lorz , E. ; Russel , R. B. ; Smith , F. M. The addition of secondary amines to some α-benzal ketones. J. Am. Chem. Soc. 1955, 77, 624–628.
  • (a) Braude , E. A. ; Forbes , W. F. ; Goften , B. F. ; Houghton , R. B. ; Waight , E. S. Alkenylation with lithium alkenyls, part XIV: Syntheses in the cyclooctene series . J. Chem. Soc. 1957 , 4711 – 4719 ; (b) Farrel , P. G. ; Read , E. A. Synthesis and spectra of some diarylidenecyclanones . Can. J. Chem. 1968 , 46 , 3685 – 3690 .
  • (a) Poornachandran , M. ; Muruganantham , R. ; Raghunathan , R. Regioselective synthesis of novel spirooxindolo and spiroindano nitro pyrrolidines through 3 + 2 cycloaddition reaction . Synth. Commun. 2006 , 36 , 141 – 150 ; (b) Poornachandran , M. ; Raghunathan , R. Synthesis of spirooxindolo/spiroindano nitro pyrrolizidines through regioselective azomethine ylide cycloaddition reaction . Synth. Commun. 2007 , 37 , 2507 – 2517 .
  • Mamta , B. ; Gayathri , D. ; Velmurugan , D. ; Ravikumar , K. ; Poornachandran , M. 4′-(4-Chlorophenyl)-1′-methylcycloheptane-1-spiro-3′-pyrrolidine-2′-spiro-2″-indan-2,1″,3″-trione . Acta Crysallogr. 2007 , E63 , o2230 – o2232 .
  • Ganesh Kumar , R. ; Gayathri , D. ; Velmurugan , D. ; Ravikumar , K. ; Poornachandran , M. 1′-Methyl-4′-phenyl-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-1″-cyclooctane-2(3H),2″-dione . Acta Crysallogr. 2006 , E62 , o4821 – o4823 .
  • Selvanayagam , S. ; Devi , M. N. ; Velmurugan , D. ; Ravikumar , K. ; Poornachandran , M. 1′-Methyl-4′-phenylindan-2-spiro-2′-pyrrolidine-3′-spiro-1″-cyclooctane-1,3,2″-trione . Acta Crystallogr. 2006 , E62 , o5551 – o5553 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.