Reaction of N-propargylic β-enaminones with acetylene dicarboxylates: Catalyst-free synthesis of 3-azabicyclo[4.1.0]hepta-2,4-dienes

RSC Advances

Volumn 4, Issue 40, 2014, Pages 21054-21059

  Goutham, Kommuru ^a,b   Nagaraju, Vemu ^a   Suresh, Surisetti ^a   Raghavaiah, Pallepogu ^c,d   Karunakar, Galla V ^a,b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

^c UNIVERSITY OF HYDERABAD   (India)

^d DR H S GOUR UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; OLEFINS;

BASE-FREE; CATALYST-FREE SYNTHESIS; DICARBOXYLATES; ENAMINONES; SINGLE-STEP;

CARBOXYLATION;

EID: 84901296919     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra00136b     Document Type: Article

References (64)

1. D. Ayres and J. D. Loike, Chemistry and pharmacology of natural products. Lignans: chemical, biological and clinical properties, Cambridge University Press, Cambridge, 1990
2. Comprehensive Heterocyclic Chemistry II, ed., A. R. Katritzky, C. W. Ress, and, E. F. V Scriven, Pergamon: Oxford, U. K., 1996, vol. 1-9
3. T. Eicher and S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, Wiley-VCH, Weinheim, Germany, 2nd edn, 2003
4. M. Saleem H. J. Kim M. S. Ali Y. S. Lee Nat. Prod. Rep. 2005 22 696
5. E. J. Kang E. Lee Chem. Rev. 2005 105 4348
6. G. M. Cragg D. J. Newman Expert Opin. Invest. Drugs 2000 9 2783
7. E. J. Kang E. Lee Chem. Rev. 2005 105 4348
8. A. Bermejo B. Figadere M.-C. Zafra-Polo I. Barrachina E. Estornell D. Cortes Nat. Prod. Rep. 2005 22 269
9. E. G. Brown, Ring Nitrogen and Key Biomolecules: The Biochemistry of N-heterocycles, Kluwer Academic, Boston, 1998
10. Comprehensive Heterocyclic Chemistry III, ed., A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, and, R. J. K. Taylor, Pergamon: Oxford, U. K., 2008, vol. 1-13
11. K. C. Majumdar G. V. Karunakar B. Sinha Synthesis 2012 44 2475
12. Z. Ye L. Shi X. Shao X. Xu Z. Xu Z. Li J. Agric. Food Chem. 2013 61 312
13. J. W. Daly T. F. Spande H. M. Garraffo J. Nat. Prod. 2005 68 1556
14. L. Malet-Sanz F. Susanne J. Med. Chem. 2012 55 4062
15. J. L. Dongl J. D. G. Jones Nature 2001 411 826
16. A. Thomas Angew. Chem., Int. Ed. 2010 49 8328
17. Metal-Catalyzed Cross-Coupling Reactions, ed., A. d. Meijere, and, F. Diederich, Wiley-VCH, Weinheim, Germany, 2nd edn, 2004
18. F. Diederich and P. J. Stang, Metal-catalyzed cross-coupling reactions, Wiley-VCH, New York, 1998
19. J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, U. K., 2000
20. B. Cornils and W. A. Hermann, Applied Homogeneous Catalysis with Organometallic Compounds, Wiley, Weinheim, Germany, 1999
21. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987
22. X.-F. Wu H. Neumann M. Beller Chem. Rev. 2013 113 1
23. K. C. Bishop III Chem. Rev. 1976 76 461
24. M. Rudolph A. S. K. Hashmi Chem. Commun. 2011 47 6536
25. E.-i. Negishi and A. d. Meijere, Handbook of organopalladium chemistry for organic synthesis, Wiley-Interscience, New York, 2002
26. D. A. Evans and J. S. Johnson, in Comprehensive Asymmetric Catalysis, ed., E. N. Jacobsen, A. Pfaltz, and, H. Yamamoto, Springer, Berlin, 1999, vol. III, p. 1177
27. L. Anastasia and E.-i. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, 2002, vol. 1, p. 311
28. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, ed., A. Berkessel, and, H. Gröger, Wiley-VCH, Weinheim, 2005
29. Enantioselective Organocatalysis, ed., P. I. Dalko, Wiley-VCH, Weinheim, 2007
30. P. I. Dalko L. Moisan Angew. Chem., Int. Ed. 2004 43 5138
31. M. Terada and N. Momiyama, in Science of synthesis: asymmetric organocatalysis, ed., K. Markova, Georg Thieme Verlag, Stuttgart, 2012, vol. 2, p. 219
32. R. A. D. Arancon C. S. K. Lin C. Vargas R. Luque Org. Biomol. Chem. 2014 12 10
33. V. P. Mehta B. Punji RSC Adv. 2013 3 11957
34. R. Hofer J. Bigorra Green Chem. 2007 9 203
35. R. V. Edwankar C. R. Edwankar O. A. Namjoshi J. R. Deschamps J. M. Cook J. Nat. Prod. 2012 75 181
36. B. Stanovnik J. Svete Chem. Rev. 2004 104 2433
37. T. Miura Y. Funakoshi M. Morimoto T. Biyajima M. Murakami J. Am. Chem. Soc. 2012 134 17440
38. The Chemistry of Enamines, ed., Z. Rappoport, John Wiley & Sons, New York, 1994, part 1, p. 525
39. Z. Chen J. Zhu H. Xie S. Li Y. Wu Y. Gong Chem. Commun. 2010 46 2145
40. R.-L. Yan J. Luo C.-X. Wang C.-W. Ma G.-S. Huang Y.-M. Liang J. Org. Chem. 2010 75 5395
41. A. Saito T. Konishi Y. Hanzawa Org. Lett. 2010 12 372
42. S. Cacchi G. Fabrizi E. Filisti Org. Lett. 2008 10 2629
43. K. Goutham N. S. V. M. R. Mangina S. Suresh P. Raghavaiah G. V. Karunakar Org. Biomol. Chem. 2014 12 2869
44. M. Rudolph A. S. K. Hashmi Chem. Soc. Rev. 2012 41 2448
45. A. S. K. Hashmi G. J. Hutchings Angew. Chem., Int. Ed. 2006 45 7896
46. S. Patai, in The Chemistry of the Cyclopropyl Group, part 2, John Wiley & Sons, New York, 1987, vol. 1
47. H. Y. Kim P. J. Walsh Acc. Chem. Res. 2012 45 1533
48. F. Brackmann A. d. Meijere Chem. Rev. 2007 107 4493
49. H. Doucet Eur. J. Org. Chem. 2008 2013
50. M. Rubin M. Rubina V. Gevorgyan Chem. Rev. 2007 107 3117
51. Y. Todo H. Takagi F. Iino Y. Fukuorka Y. Ikeda K. Tanaka I. Saikawa H. Narita Chem. Pharm. Bull. 1994 42 2049
52. A. W. Ludger W. Brandt Chem. Rev. 2003 103 1625
53. S. Gomi D. Ikeda H. Nakamura H. Naganawa F. Yamashita K. Hotta S. Kondo Y. Okami H. Umezawa Y. Iitaka J. Antibiot. 1984 37 1491
54. J. Pietruszka Chem. Rev. 2003 103 1051
55. P. J. Dunn RSC Drug Discovery Ser. 2011 9 117
56. B. Halton Chem. Rev. 2003 103 1327
57. F. Gnad O. Reiser Chem. Rev. 2003 103 1603
58. K. J. Butcher S. M. Denton S. E. Field A. T. Gillmore G. W. Harbottle R. M. Howard D. A. Laity C. J. Ngono B. A. Pibworth Org. Process Res. Dev. 2011 15 1192
59. R. Schiess J. Gertsch W. B. Schweizer K.-H. Altmann Org. Lett. 2011 13 1436
60. N. Ty R. Pontikis G. G. Chabot E. Devillers L. Quentin S. Bourg J.-C. Florent Bioorg. Med. Chem. 2013 21 1357
61. H. Pellisier Tetrahedron 2008 64 7041
62. P. Tang Y. Qin Synthesis 2012 44 2969
63. R. Bambal H. Friz G. Rihs T. Tschamber J. Streith Angew. Chem., Int. Ed. 1987 26 668
64. F. Micheli P. Cavanni D. Andreotti R. Arban R. Benedetti B. Bertani M. Bettati L. Bettelini G. Bonanomi S. Braggio R. Carletti A. Checchia M. Corsi E. Fazzolari S. Fontana C. Marchioro E. Merlo-Pich M. Negri B. Oliosi E. Ratti K. D. Read M. Roscic I. Sartori S. Spada G. Tedesco L. Tarsi S. Terreni F. Visentini A. Zocchi L. Zonzini R. D. Fabio J. Med. Chem. 2010 53 4989