A cascade thermal isomerisation of cyclobutane di-(carbomethoxy) Δ 2-1,2,3-triazolines with intramolecular 1,3-dipolar cycloreversion as the key step

Tetrahedron

Volumn 68, Issue 16, 2012, Pages 3306-3318

  Margetić, Davor ^a   Warrener, Ronald N ^b   Butler, Douglas N ^b   Jin, Chuan Ming ^b  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b CENTRAL QUEENSLAND UNIVERSITY   (Australia)

Author keywords

Computational chemistry; Cycloreversion; Dipolar cycloaddition; Nitrogen heterocycles; Reaction mechanism; Rearrangement

Indexed keywords

1,2,7 TRIAZA [3.3.0]OCTA 2 ENE; CYCLOBUTANE; HYDROGEN; NORBORNANE DERIVATIVE; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; ISOMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; RING CLOSING METATHESIS;

EID: 84859159558     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.073     Document Type: Article

References (50)

1. J. March Advanced Organic Chemistry: Reactions, Mechanisms and Structure 6th ed. 2007 John Wiley & Sons New York, NY
2. P. Scheiner J. Org. Chem. 30 1965 7 10
3. D.S. Reddy, W.R. Judd, and J. Aubé Org. Lett. 5 2003 3899 3902
4. T. Gilchrist, and M.J. Alves S. Brase, K. Banert, Organic Azides Syntheses and Applications 2010 Wiley Chichester, UK 177
5. J. Perrocheau, R. Carri, and J.-P. Fleury Can. J. Chem. 72 1994 2458 2467
6. W. Broeckx, N. Overbergh, C. Samyn, G. Smets, and G. L'Abb Tetrahedron 27 1971 3527 3534
7. G. Le Hetet, R. Danion-Bougot, and R. Carri Bull. Soc. Chim. Belg. 106 1996 259 272
8. M.S. Ouali, M. Vaultier, and R. Carrie Bull. Soc. Chim. Fr. 1979 634 645
9. D. Pocar, P. Trimarco, and G. Bombieri J. Heterocycl. Chem. 35 1998 687 693
10. D. Pocar, E. Roversi, P. Trimarco, and G. Valgattarri Liebigs Ann./Recl. 1995 487 493
11. Y. Kobayashi, A. Ando, K. Kawada, A. Ohsawa, and I. Kumadaki J. Org. Chem. 45 1980 2962 2966
12. M. Christl, S. Lesch, S. Deuerlein, and D. Stalke Helv. Chim. Acta 88 2005 1421 1430
13. M. Franck-Neumann, and G. Buchecker Tetrahedron Lett. 10 1969 2659 2662
14. T. Mitsudo, K. Kokuryo, T. Shinsugi, Y. Nakagawa, Y. Watanabe, and Y. Takegami J. Org. Chem. 44 1979 4492 4496
15. D. Margetić, P. Trošelj, and Y. Murata Synth. Commun. 41 2011 1239 1246
16. G.T. Anderson, J.R. Henry, and S.M. Weinreb J. Org. Chem. 56 1991 6946 6948
17. D.N. Butler, J.R. Malpass, D. Margetić, R.A. Russell, G. Sun, and R.N. Warrener Synlett 1998 588 589
18. R.N. Warrener Eur. J. Org. Chem. 2000 3363 3380
19. D.N. Butler, M.L.A. Hammond, M.R. Johnston, G. Sun, J.R. Malpass, J. Fawcett, and R.N. Warrener Org. Lett. 2 2000 721 724
20. C.H. Heathcock Proc. Natl. Acad. Sci. U.S.A. 93 1996 14323 14327
21. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. Engl. 105 1993 137 170
22. L.F. Tietze Chem. Rev. 96 1996 115 136
23. K.K. Wang Chem. Rev. 96 1996 207 222
24. Wagner, G.; Pedersen, B.; Herrmann, R. Article 42. In Electronic Conference on Organometallic Chemistry (ECTOC-3), 30 June-31 July 1997, Rzepa, H.; Goodman, J.; Winter, M., Eds. http://www.ch.ic.ac.uk/ectoc/ectoc-3/pub/042/.
25. D. Margetić, D.N. Butler, R.N. Warrener, and C.M. Holland The Second Brisbane Biological and Organic Chemistry Symposium (BBOCS-2) November 30, 2001 The University of Queensland Brisbane, Australia
26. R.N. Warrener, D. Margetić, D.N. Butler, and G. Sun Synlett 2001 202 205
27. D. Margetić, D.N. Butler, and R.N. Warrener Aust. J. Chem. 53 2000 959 963
28. A. Dastan, E. Uzundumlu, M. Balci, F. Fabris, and O. De Lucchi Eur. J. Org. Chem. 2004 183 192
29. V.G. Bianchi, C. De Micheli, and R. Gandolfi Angew. Chem., Int. Ed. Engl. 18 1979 781 798
30. G. Mloston, and R. Huisgen Tetrahedron 57 2001 145 151
31. T. Oshima, and T. Nagai J. Chem. Soc., Chem. Commun. 1994 2787 2788
32. B.F. Lira, P.F. de Athayde Filho, J. Miller, A.M. Simas, A. de Farias Dias, and M.J. Vieira Molecules 7 2002 791 800
33. N. Kumagai, S. Matsunaga, and M. Shibasaki Angew. Chem., Int. Ed. 43 2004 478 482
34. H.-J. Gais, M. van Gumpel, G. Raabe, J. Müller, S. Braun, H.J. Lindner, S. Rohs, and J. Runsink Eur. J. Org. Chem. 1999 1627 1651
35. M.N. Paddon-Row, D.N. Butler, and R.N. Warrener J. Chem. Soc., Chem. Commun. 1976 741 747
36. J.K. Stille, W.A. Feld, and M.E. Freeburger J. Am. Chem. Soc. 94 1972 8485 8489
37. D. Margetić T. Ishikawa, Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts 2009 Wiley Chichester, UK 9 48
38. A. de Cózar, M.C. Millán, C. Cebrián, P. Prieto, A. Díaz-Ortiz, A. de la Hoz, and F.P. Cossío Org. Biomol. Chem. 8 2010 1000 1009
39. S. Yamabe, N. Tsuchida, and Y.J. Yamazaki Chem. Theor. Comput. 1 2005 944 952
40. A.S. Morkovnik, L.N. Divaeva, A.I. Uraev, K.A. Lyssenko, R.K. Mamin, I.G. Borodkina, G.S. Borodkin, A.S. Burlov, and A.D. Garnovskii Russ. Chem. Bull., Int. Ed. 57 2008 1496 1507
41. J.E. Norton, B.H. Northrop, C. Nuckolls, and K.N. Houk Org. Lett. 8 2006 4915 4918
42. D.J. Cram, and R.T. Uyeda J. Am. Chem. Soc. 84 1962 4358 4359
43. A. Padwa Angew. Chem., Int. Ed. Engl. 15 1976 123 136
44. C.-H. Yang, H.-J. Shen, R.-H. Wang, and J.-C. Wang J. Chin. Chem. Soc. 49 2002 95 102
45. P.K. Kadaba, B. Stanovnik, and M. Tišler A.R. Katritzky, Advances in Heterocyclic Chemistry Vol. 37 1984 Academic Orlando, FL 323
46. G. Szeimies, and R. Huisgen Chem. Ber. 99 1966 491 503
47. R.N. Warrener, M.L.A. Hammond, and D.N. Butler Synth. Commun. 31 2001 1167 1175
48. D. Margetić Microwave Assisted Cycloaddition Reactions 2011 Nova Science New York, NY
49. D. Lecoq, B.A. Chalmers, R.N. Veedu, D. Kvaskoff, P.V. Bernhardt, and C. Wentrup Aust. J. Chem. 62 2009 1631 1638
50. N.S. Wilson, C.R. Sarko, and G.P. Roth Tetrahedron Lett. 43 2002 581 583