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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 7
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Original Articles

Novel One Pot Regioselective Multicomponent Synthesis of Highly Functionlaized Spiro Pyrrolidines Through 1,3-Dipolar Cycloaddition Approach

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Pages 1041-1054 | Received 20 May 2011, Published online: 07 Jan 2013

REFERENCES

  • (a) Nair , V. ; Rajesh , C. ; Vinod , A. U. ; Bindu , S. ; Sreekanth , A. R. ; Mathen , J. S. ; Balagopal , L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes . Acc. Chem. Res. 2003 , 36 , 899 – 907 ; (b) Domling , A. ; Ugi , I. Multicomponent reactions with isocyanides . Angew. Chem. Int. Ed. 2000 , 39 , 3168 – 3210 ; (c) Orru , R. V. A. ; de Greef , M. Recent advances in solution phase multicomponent methodology for the synthesis of heterocyclic compounds . Synthesis 2003 , 1471 – 1499 .
  • (a) Karthikeyan , K. ; Perumal , P. T. ; Etti , S. ; Shanmugam , G. Diasteroselective synthesis of pyrazolyl isoxalidines via 1,3-dipolar cycloaddition . Tetrahedron 2007 , 63 , 10581 – 10586 ; (b) Domling , A. Recent developments in isocyanide based multicomponent reactions in applied chemistry . Chem. Rev. 2006 , 106 , 17 – 89 ; (c) Devi , I. ; Kumar , B. S. D. ; Bhuyan , P. J. A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state . Tetrahedron Lett. 2003 , 44 , 8307 – 8310 ; (d) Feliu , L. ; Vera-Luque , P. ; Albericio , F. ; Álvarez , M. Advances in solid-phase cycloadditions for heterocyclic synthesis . J. Comb. Chem. 2007 , 9 , 521 – 565 ; (e) Zhu , J. Recent developments in the isonitrile-based multicomponent synthesis of heterocycles . Eur. J. Org. Chem. 2003 , 1133 – 1144 ; (f) Mohammadi , A. A. ; Dabiri , M. ; Qaraat , H. A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′ quinazoline]-3,4′(3′H)-dione derivatives . Tetrahedron 2009 , 65 , 3804 – 3808 .
  • (a) Galliford , C. V. ; Scheidt , K. A. Pyrrolidinyl-spirooxindole natural products as inspirations for the developments of potential therapeutic agents . Angew. Chem., Int. Ed. 2007 , 46 , 8748 – 8758 ; (b) Bindra , J. S. The Alkaloids, Vol. 14; R. H. F. Manske (Eds.); Academic Press: New York, 1973,; p. 84 .
  • (a) Dandia , A. ; Singh , R. ; Khaturia , S. ; Merienne , C. ; Morgant , G. ; Loupy , A. Efficient microwave-enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro[indole-thiazolidinones]as potent antifungal agents and crystal structure of spiro[3H-indole-3,2′-thiazolidine]-3′(1,2,4-triazol-3-yl)-2,4'(1H)-dione. Bioorg. Med. Chem. 2006, 14, 2409–2417; (b) Ding , K. ; Lu , Y. ; Nikolovska-Coleska , Z. ; Qiu , S. ; Ding , Y. ; Gao , W. ; Stuckey , J. ; Krajewski , K. ; Roller , P. P. ; Tomita , Y. ; Parrish , D. A. ; Deschamps , J. R. ; Wang , S. Structure based design of potent non-peptide MDM2 inhibitors. J. Am. Chem. Soc. 2005, 127, 10130–10131.
  • (a) Lo , M. M.-C. ; Neumann , C. S. ; Nagayama , S. ; Perlstein , E. O. ; Schreiber , S. L. A library of spirooxindoles based on a stereoselective three-component coupling reaction . J. Am. Chem. Soc. 2004 , 126 , 16077 – 16086 ; (b) Marti , C. ; Carreira , E. M. Construction of spiro[pyrrolidine-3, 3′-oxindoles]-Recent applications to the synthesis of oxindole alkaloids . Eur. J. Org. Chem. 2003 , 2209 – 2219 ; (c) Dounary , A. B. ; Hatanaka , K. ; Kodanko , J. J. ; Oestreich , M. ; Overman , L. E. ; Pfeifer , L. A. ; Weiss , M. M. Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents: Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular Heck reactions . J. Am. Chem. Soc. 2003 , 125 , 6261 – 6271 , and references therein (d) Lin , H. ; Danishefsky , S. J. Gelsemine–A thought provoking target for total synthesis . Angew. Chem. Int. Ed. 2003 , 42 , 36 – 51 .
  • Skiles , J. W. ; McNeil , D. Spiro indolinone β-lactams, inhibitors of poliovirus and rhinovirus 3C-proteinases . Tetrahedron Lett. 1990 , 31 , 7277 – 7280 .
  • (a) Basavaiah , D. ; Reddy , B. S. ; Badsara , S. S. Recent contributions from the Baylis–Hillman reaction to organic chemistry . Chem. Rev. 2010 , 110 , 5447 – 5674 ; (b) Basavaiah , D. ; Rao , P. D. ; Hyma , R. S. The Baylis–Hillman reaction a novel carbon–carbon bond-forming reaction Tetrahedron 1996 , 52 , 8001 – 8062 ; (c) Basavaiah , D. ; Rao , A. J. ; Satyanarayana , T. Recent advances in the Baylis–Hillman, reaction and applications . Chem. Rev. 2003 , 103 , 811 – 892 .
  • (a) Cho , C.-W. ; Krische , M. J. Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita–Baylis–Hillman acetates: An organocatalytic allylic alkylation . Angew. Chem., Int. Ed. 2004 , 43 , 6689 – 6691 ; (b) Kabalka , F. W. ; Venkataiah , B. ; Dong , G. Pd-catalyzed cross-coupling of Baylis–Hillman acetate adducts with bis(pinacolato)diboron: An efficient route to functionalized allyl borates . J. Org. Chem. 2004 , 69 , 5807 – 5809 .
  • (a) Hoffman , H. M. R. ; Rabe , J. Synthesis and biological activity of α-methylene-γ-butyrolactones . Angew. Chem. Int. Ed. 1985 , 24 , 94 – 110 ; (b) 1,3-Dipolar Cycloaddition Chemistry A. Padwa (Ed.); Wiley: New York, 1984; Vols. 1 and 2; (c) Tsuge , O. ; Kanemasa , S. In Advances in Heterocyclic Chemistry; A. R. Katritzky (Ed.); Academic Press: San Diego, 1989; Vol. 45; pp. 231–252; (d) Advances in Cycloaddition R. Grigg, V. Sridharan, D. P. Curran, (Eds.); Jai Press: London, 1993; Vol. 3; pp. 161–180; (e) Kathiravan , S. ; Ramesh , E. Synthesis of pyrrolo[2,3-a]pyrrolizine and pyrrolizine[2,3-a]pyrrolizine derived from allyl derivatives of Baylis–Hillman adducts through intramolecular 1,3-dipolar cycloaddition. Tetrahedron Lett. 2009, 50, 2389–2391.
  • (a) Liddel , J. R. Pyrrolizidine alkaloids . Nat. Prod. Rep. 1996 , 13 , 187 – 194 .
  • (a) Hartmann , T. ; Witte , L. Chemistry, biology and chemoecology of pyrrolizidine alkaloids . In Alkaloids: Chemical and Biological Perspectives ; S. W. Pelletier (Ed.); Pergamon Press : Oxford , 1995 , Vol. 9 ; (b) Rajeswaran , W. G. ; Labroo , R. B. ; Cohen , E. A. Synthesis of 5-[(indol-2-on-3-yl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-diones and spirocyclopropyloxindole derivatives potential aldose reductase inhibitors. J. Org. Chem. 1999, 64, 1369–1371.
  • (a) Katritzky , A. R. C. ; Rees , W. ; Scriven , E. F. V. Comprehensive Heterocyclic Chemistry , Pregamon Press , Oxford , 1996 , Vol. 3 , p. 77 ; (b) Kruse , L. I. ; Hansch , C. ; Sammes , P. G. ; Taylor , J. B. Comprehensive Medicinal Chemistry , Pregamon Press : Oxford , 1990 , Vol. 2 , p. 123 ; (c) Hai , L. ; Guolan , D. ; Daqing , S. Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides. J. Comb. Chem. 2010, 12, 633–637.
  • White , A. W. ; Almassy , R. ; Calvert , A. H. ; Curtin , N. J. ; Griffin , R. J. ; Hostomsky , Z. ; Maegley , K. ; Newell , D. R. ; Srinivasan , S. ; Golding , B. T. Resistance-modifying agents, 9: Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose)polymerase. J. Med. Chem. 2000, 43, 4084–4097.
  • (a) Jones , C. D. ; Winter , M. A. ; Hirsch , K. S. ; Stamm , N. ; Taylor , H. M. ; Holden , H. E. ; Davenport , J. D. Estrogen synthetase inhibitors, 2: Comparison of the invitro aromatase inhibitory activity for a variety of nitrogen heterocycles substituted with diarylmethane or diarylmethanol groups . J. Med. Chem. 1990 , 33 , 416 – 429 .
  • (a) Kathiravan , S. ; Raghunathan , R. A facile one-pot three-component synthesis of macrocyclic imidazolidines by [3 + 2] cycloaddition reaction of azomethine ylides . Synlett 2009 , 1126 – 1129 ; (b) Suresh Babu , A. R. ; Raghunathan , R. ; Satiskumar , B. K. A facile synthesis of ferrocene grafted N-methyl spiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides . Tetrahedron Lett. 2009 , 50 , 2818 – 2821 ; (c) Suresh Babu , A. R. ; Raghunathan , R. An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides . Tetrahedron Lett. 2008 , 49 , 4618 – 4620 .
  • Selvanayagam , S. ; Sridhar , B. ; Ravikumar , K. ; Kathiravan , S. ; Raghunathan , R. Methyl 3-[(1H-benzimidazol-1-yl)methyl]-1-methyl-4-(4-methylphenyl)-2′-oxopyrrolidine-2-spiro-3′-1-benzimidazole-3-carboxylate . Acta Cryst. 2010 , E66 , o2508 – 2509 .

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