Orthogonal synthesis of isoindole and isoquinoline derivatives from organic azides

Organic Letters

Volumn 11, Issue 3, 2009, Pages 729-732

  Hui, Benjamin Wei Qiang ^a   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 62149120526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802816k     Document Type: Article

References (55)

1. (a) Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247.
2. (b) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed; Wiley-Interscience: New York, 1984; Vol. 2, p 316.
3. (c) Feldman, K. S.; Iyer, M. R.; López, C. S.; Faza, O. N. J. Org. Chem. 2008, 73, 5090.
4. (d) Zhou, Y.; Murphy, P. V. Org. Lett. 2008, 10, 3777.
5. (e) Kim, S.; Lee, Y. M.; Lee, J.; Lee, T.; Fu, Y.; Song, Y.; Cho, J.; Kim, D. J. Org. Chem. 2007, 72, 4886.
6. (f) Huang, X.; Shen, R.; Zhang, T. J. Org. Chem. 2007, 72, 1534.
7. (g) Feldman, K. S.; Iyer, M. R.; Hester, D. K., H. Org. Lett. 2006, 8, 3116.
8. (h) Feldman, K. S.; Iyer, M. R. J. Am. Chem. Soc. 2005, 127, 4590.
9. (i) Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27.
10. (j) Liu, J.-M; Young, J.-J.; Li, Y.-J.; Sha, C.-K. J. Org. Chem. 1986, 51, 1120.
11. (k) Sundberg, R. J.; Pearce, B. C. J. Org. Chem. 1982, 47, 725.
12. (l) Smith, P. A. S.; Chou, S. P. J. Org. Chem. 1981, 46, 3970, and references therein.
13. For reviews of 6π-electrocyclization, see: (a) Okamura, W. H.; de Lera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 5, p 699.
14. (b) Marvell, E. N. Thermal Electrocyclic Reactions; Academic Press: New York, 1980.
15. For recent examples of 6π-electrocyclization of azatriene, see: (a) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602.
16. (b) Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918.
17. (c) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645.
18. (d) Meketa, M. L.; Weinreb, S. M.; Nakao, Y.; Fusetani, N. J. Org. Chem. 2007, 72, 4892.
19. (e) Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099, and references therein.
20. (a) Mi, B.-X.; Wang, P.-F.; Liu, M.-W.; Kwong, H.-L.; Wong, N.-B.; Lee, C.-S.; Lee, S.-T. Chem. Mater. 2003, 15, 3148.
21. (b) Ding, Y.; Hay, A. S. J. Polym. Sci. Part A: Polym. Chem. 1999, 37, 3293.
22. (c) Gauvin, S.; Sanierte, F.; Dodelet, J. P.; Ding, Y.; Hlil, A. R.; Hay, A. S.; Anderson, J.; Armstrong, N. R.; Gorjanc, T. C.; D'lorio, M. Thin Sold Films 1999, 353, 218.
23. (d) Matuszewski, B. K.; Givens, R. S.; Srinivasachar, K.; Carlson, R. G.; Higuchi, T. Anal. Chem. 1987, 59, 1102.
24. (e) Zweig, A.; Metzler, G.; Maurer, A.; Roberts, B. G. J. Am. Chem. Soc. 1967, 89, 4091.
25. (a) Duan, S.; Sinha-Mahapatra, D. K.; Herndon, J. W. Org. Lett. 2008, 10, 1541.
26. (b) Chen, Y.-L.; Lee, M.-H.; Wong, W.-Y.; Lee, A. W. M. Syntlett 2006, 2510.
27. (c) Chen, Z.; Müller, P.; Swager, T. M. Org. Lett. 2006, 8, 273.
28. (d) LeHoullier, C. S.; Gribble, G. W. J. Org. Chem. 1983, 48, 2364.
29. For reports on the mechanism of the elimination of dinitrogen from triazoline intermediates with heterolytic cleavage of the N-N bond, see: (a) Shea, K. J.; Kim, J.-S. J. Am. Chem. Soc. 1992, 114, 4864.
30. (b) Wladkowski, B. D.; Smith, R. H., Jr.; Michejda, C. J. J. Am. Chem. Soc. 1991, 113, 7893, and references therein.
31. A radical pathway via homolytic cleavage of the N-N bond of triazoline intermediates is also proposed, for examples, see referenceslc,g,h and: Broeckx, W.; Overbergh, N.; Samyn, C.; Smets, G.; L'abbé, G. Tetrahedron 1971, 27, 3527.
32. One of the most common synthetic methods of isoindoles are the reactions of phthalaldehyde and amine in the presence of reductants or nucleophiles. For examples, see: (a) Watanabe, Y.; Shim, S. C.; Uchida, H.; Mitsudo, T.; Takegami, Y. Tetrahedron 1979, 55, 1433.
33. (b) Simons, S. S., Jr.; Johnson, D. F. J. Chem. Soc., Chem. Commun. 1977, 374.
34. (c) Bonnett, R.; Brown, R. F. C. J. Chem. Soc., Chem. Commun. 1972, 393.
35. For recent reports on isoindole formation by the other methods, see: (a) Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040.
36. (b) Kadzimirsz, D.; Hildebrandt, D.; Merz, K.; Dyker, G. Chem. Commun. 2006, 661.
37. (c) Murashima, T.; Tamai, R.; Nishi, K.; Nomura, K.; Fujita, K.; Uno, H.; Ono, N. J. Chem. Soc., Perkin Trans. 1 2000, 995.
38. (d) Dialer, H.; Polborn, K.; Beck, W. J. Organomet. Chem. 1999, 589, 21.
39. The structure of 2a was secured by X-ray crystallographic analysis (see Supporting Information). CCDC-710407 contains the supplementary crystallographic data for compound 2a. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/ conts/retrieving.html.
40. The introduction of a carbonyl moiety at the C1-position on isoindoles is indispensable for this isoindole formation. For an example, the reaction of 2′-vinylbenzyl azide under same reaction conditions gave a complex mixture without desired isoindoles.
41. The starting materials were prepared by almost the same procedures as Scheme 2; see Supporting Information.
42. For recent reviews on isoqunoline derivatives, see: (a) Keller, P. A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008; Vol. 7, p 217.
43. (b) Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, 1996; Vol. 5, p 167.
44. (c) Blently, K. W. Nat. Prod. Rep. 2006, 23, 444.
45. (d) Kartsev, V. G. Med. Chem. Res. 2004, 13, 325.
46. (e) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
47. 3) is almost same as that of NaOAc (HOAc).
48. For generation of imine from α-azido ketones and esters under the strong basic conditions, see: (a) Manis, P. A.; Rathke, M. W. J. Org. Chem. 1980, 45, 4952.
49. (b) Edwards, O. E.; Purushothaman, K. K. Can. J. Chem. 1964, 42, 712.
50. For preparation of isoquinoline by 6π-electrocyclization of oxime derivatives, see: Kumemura, T.; Chosi, T.; Yukawa, J.; Hirose, A.; Nobuhiro, J.; Hibino, S. Heterocycles 2005, 66, 87.
51. 6π-Electrocyclization of 1-azatriene possessing N-H imine moiety is quite rare. For an example, see: Jutz, C.; Lobering, H.-G.; Trinkl, K.-H. Synthesis 1977, 326.
52. 2O (10 equiv) can be used as a proton source, giving dihydroisoquinoline 6a in 88% yield from azide 1a.
53. Curtin, D. Y.; Crew, M. C. J. Am. Chem. Soc. 1955, 77, 354.
54. The structure of 6f was secured by X-ray crystallographic analysis (see Supporting Information). CCDC-710406 contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/conts/retrieving.html.
55. The ring-opening reactions to lead isoquinolines 6f' and 6g seem to occur just after 6π-electrocyclization, not from the corresponding dihydroisoquinolines like 6f. The detailed investigation is discussed in Supporting Information.