Tandem [8 + 2] cycloaddition-[2 + 6 + 2] dehydrogenation reactions involving imidazo[1,2- a ]pyridines and imidazo[1,2- a ]pyrimidines

Journal of Organic Chemistry

Volumn 75, Issue 9, 2010, Pages 2776-2784

  Aginagalde, Maialen ^a   Vara, Yosu ^b   Arrieta, Ana ^a   Zangi, Ronen ^a,c   Cebolla, Vicente L ^d   Delgado Camón, Arantzazu ^d   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b Ikerchem Ltd   (Spain)

^c BASQUE FOUNDATION FOR SCIENCE   (Spain)

^d INSTITUTO DE CARBOQUÍMICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROGENATION; MICROWAVE IRRADIATION;

BLUE LIGHT; DEHYDROGENATION REACTIONS; INDOLIZINES; PHOTOPHYSICAL PROPERTIES; REGIOCONTROL; SUBSTITUTION PATTERNS; TRANSITION STRUCTURES; TRIMETHYLSILYL;

PYRIDINE;

2 (TRIMETHYLSILYL)PHENYL TRIFLATE; BENZENE DERIVATIVE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; IMIDAZO[1,2 A]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BLUE LIGHT; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DEHYDROGENATION; MICROWAVE IRRADIATION; PRECURSOR; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 77951795479     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9022815     Document Type: Article

References (62)

1. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781-853
2. Nair, V.; Abhilash, K. G. Synlett 2008, 301-312
3. Sankararaman, S. Pericyclic Reactions -A Textbook; Wiley-VCH: Weinheim, 2005; pp 193 - 196.
4. Doering, W. v. E.; Wiley, D. W. Tetrahedron 1960, 11, 183-198
5. Rigby, J. H.; Ahmed, G.; Ferguson, M. D. Tetrahedron Lett. 1993, 34, 5397-5400
6. Rigby, J. H.; Pigge, F.-C.; Ferguson, M. D. Tetrahedron Lett. 1994, 35, 8131-8132
7. Machiguchi, T.; Yamabe, S. Tetrahedron Lett. 1990, 31, 4169-4172
8. Ito, K.; Saito, K.; Takahashi, K. Bull. Chem. Soc. Jpn. 1992, 65, 812-816
9. Nair, V.; Abhilash, K. G. Tetrahedron Lett. 2006, 47, 8707-8709
10. Farrant, G. C.; Feldman, R. Tetrahedron Lett. 1970, 11, 4979-4982
11. See, for example: Galbraith, A.; Small, T.; Barnes, R. A.; Bockelheide, V. J. Am. Chem. Soc. 1961, 83, 453-456
12. Kuznetsov, A. G.; Bush, A. K.; Babaev, E. V. Tetrahedron 2008, 64, 749-756
13. Mitsumori, T.; Benoikov, M.; Dautel, O.; Wudl, F.; Shioya, T.; Sato, H.; Sato, Y. J. Am. Chem. Soc. 2004, 126, 16793-16803
14. Shen, Y.-M.; Grampp, G.; Leesakul, N. L.; Hu, H.-W.; Xu, J.-H. Eur. J. Org. Chem. 2007, 3718-3726
15. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084-4089
16. Zhong, G.; Chan, B.; Radom, L. J. Am. Chem. Soc. 2007, 129, 924-933
17. Vara, Y.; Aldaba, E.; Arrieta, A.; Pizarro, J. L.; Arriortua, M. I.; Cossio, F. P. Org. Biomol. Chem. 2008, 6, 1763-1772
18. Gaussian 03, Rev E.01; Frisch, M. J., Ed.; Gaussian, Inc.: Wallingford, CT, 2004.
19. Jaguar, version 7.5; Schrödinger, LLC: New York, 2008.
20. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
21. Ziegler, T. Chem. Rev. 1991, 91, 651-667
22. Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980
23. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
24. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
25. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
26. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 76 - 87 and references cited therein.
27. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445-11459
28. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
29. Chen, J.-L.; Hong, J.-T.; Wu, K.-J.; Hu, W.-P. Chem. Phys. Lett. 2009, 468, 307-312
30. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096
31. NBO 5.0: Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F., Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.
32. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926
33. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746
34. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. S. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318
35. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260
36. Borden, W. T.; Loncharich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213-236
37. Moyano, A.; Peric's, M. A.; Valentí, E. J. Org. Chem. 1989, 54, 573-582
38. Lecea, B.; Arrieta, A.; Lopez, X.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc. 1995, 117, 12321-12314
39. McIver, J. W., Jr.; Komornicki, A. J. J. Am. Chem. Soc. 1972, 94, 2625-2633
40. Car, R.; Parrinello, M. Phys. Rev. Lett. 1985, 55, 2471-2474
41. Baroni, S.; Dal Corso, A.; De Gironcoli, S.; Giannozzi, P.; Cavazzoni, C.; Ballabio, G.; Scandolo, S.; Chiarottí, G.; Focher, P.; Pasquarello, A.; Lasonen, K.; Trave, A.; Car, R.; Marzari, N.; Kokalj, A. Quantum Espresso Package 2005, http://www.quantum-espresso.org, accessed March 26, 2009.
42. Becke, A. D. J. Chem. Phys. 1992, 96, 2155-2160
43. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
44. Nosé, S. Mol. Phys. 1984, 52, 255-268
45. Hoover, W. G. Phys. Rev. A 1985, 31, 1695-1697
46. Verlet, L. Phys. Rev. 1967, 159, 98-103
47. Stowasser, R.; Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414-3420
48. Baeredens, E. J.; Gritsenko, O. V. J. Phys. Chem. A 1997, 101, 3583-5403
49. Bickelhaupt, F. M.; Baerends, E. J. In: Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Wiley-VCH: New York, 2000; Vol. 15, pp 1 - 86.
50. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842-3888
51. Bader, R. F. W. Atoms in Molecules- A Quantum Theory; Clarendon Press: Oxford, 1990; pp 12 - 52.
52. Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033-7036
53. Morao, I.; Cossío, F. P. J. Org. Chem. 1999, 64, 1868-1874
54. Cossío, F. P.; Morao, I.; Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6737-6746
55. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211-1214
56. Shi, F.; Waldo, J. P.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409-2412
57. Akai, S.; Ikawa, T.; Takayanagi, S.; Morikawa, Y.; Mori, S.; Tsubakiyama, M.; Egi, M.; Wada, Y.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 7673-7676
58. Yadav, J. S.; Reddy, B. V. S.; Rao, Y. G.; Srinivas, M.; Narsaiah, A. V. Tetrahedron Lett. 2007, 48, 7717-7720
59. Ueno, M.; Togo, H. Synthesis 2004, 16, 2673-2677
60. Katritzky, A. R.; Qiu, G.; Cong, Q.-H.; He, H.-Y.; Steel, M. J. J. Org. Chem. 2000, 65, 9201-9205
61. Xie, Y.-Y. Synth. Commun. 2005, 35, 1741-1746
62. CCDC 741416 contains the supplementary crystallographic data for compound 10c. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data- request/cif, by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Rd, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.