One-step route to 2,3-diaminopyrroles using a titanium-catalyzed four-component coupling

Organometallics

Volumn 28, Issue 13, 2009, Pages 3876-3881

  Barnea, Eyal ^a   Majumder, Supriyo ^a   Staples, Richard J ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINES; COMPONENT COUPLING; EFFICIENT PROCESS; INTERNAL ALKYNES; ISONITRILE; SELECTIVE GENERATION; SINGLE CRYSTAL X-RAY DIFFRACTION; TERMINAL ALKYNE; TITANIUM COMPLEXES;

CATALYSIS; CATALYSTS; NITROGEN COMPOUNDS; POTASSIUM COMPOUNDS; TITANIUM;

ACETYLENE;

EID: 67650296197     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9001928     Document Type: Article

References (64)

1. For a recent collection of reviews see: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: New York, 2005.
2. For selected recent examples of catalyzed multicomponent couplings to generate heterocycles see: (a) Krenske, E. H.; Houk, K. N.; Arndtsen, B. A.; St. Cyr, D. J. J. Am. Chem. Soc. 2008, 130, 10052.
3. (b) Lu, Y.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2008, 47, 5430.
4. (c) Black, D. A.; Beveridge, R. E.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1906.
5. (d) Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171.
6. (e) Isambert, N.; Lavilla, R. Chem.-Eur. J. 2008, 14, 8444.
7. (f) Church, T. L.; Byrne, C. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2007, 129, 8156.
8. (g) D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095.
9. (h) Dhawan, R.; Dghaym, R. D.; St. Cyr, D. J.; Arndtsen, B. A. Org. Lett. 2006, 8, 3927.
10. (i) Siamaki, A. R.; Arndtsen, B. A. J. Am. Chem. Soc. 2006, 128, 6050.
11. j) Mitsudo, K.; Thansandote, P.; Wilhelm, T.; Mariampillai, B.; Lautens, M. Org. Lett. 2006, 8, 3939.
12. (k) Zhu, J., Bienaymé, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005,
13. (l) Balme, G. Angew. Chem., Int. Ed. 2004, 43,6238.
14. (m) Kamijo, S.; Jin, T.; Huo, Z. B.; Yamamoto, Y. J. Org. Chem. 2004, 69, 2386.
15. (n) Kamijo, S.; Jin, T.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 689.
16. (o) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003,125, 7786.
17. (p) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441.
18. Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880.
19. (a) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
20. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
21. (c) McGrane, P. L.; Jenson, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
22. (d) Zi, G.; Blosch, L. L.; Jia, L.; Andersen, R. A. Organometallics 2005, 24, 4602.
23. (e) Poise, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405.
24. (f) Duncan, A. P.; Bergman, R. G. Chem. Ree 2002, 2, 431.
25. (g) Severin, R.; Doye, S. Chem. Soc. Rev. 2007, 36, 1407.
26. This type of metallacycle has recently been isolated. Vujkovic, N.; Fillol, J. L.; Ward, B. D.; Wadepohl, H.; Mountford, P.; Gade, L. H. Organometallics 2008, 27, 2518.
27. For a review on azadienes in synthesis see: (a) Jayakumar, S.;Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. See also:
28. (b) Calvo, L. A.; Gonzalez-Nogal, A. M.; Gonzalez-Ortega, A.; Sañudo, M. C. Tetrahedron Lett. 2001, 42, 8981, for related silyl isoxazole chemistry.
29. Formamidine can become the maj or product in cases where a very unreactive alkyne is used.
30. Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967.
31. (a) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011.
32. (b) Li, Y.; Turnas, A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2002, 41, 6298.
33. 2)2(dpma) tended to become inactive, and large quantities of starting materials remained.
34. For a general review on amino derivatives of five-membered heterocycles see: (a) Granik, V. G.; Kadushkin, A. V.; Liebscher, J. Adv. Heterocycl. Chem. 1999, 72, 79. For some selected examples of amino pyrroles see:
35. (b) De Rosa, M.; Issac, R. P.; Houghton, G. Tetrahedron Lett. 1995, 36, 9261.
36. (c) Schmuck, C.; Dudaczek, J. Tetrahedron Lett. 2005, 46, 7101.
37. (d) Demir, A. S.; Emrullahoglu, M. Tetrahedron 2005, 61, 10482.
38. (e) De Rosa, M.; Issac, R. P.; Marquez, M.; Orozco, M.; Luque, F. J.; Timken, M. D. Perkin Trans 2 1999, 1433.
39. (f) Brouillette, Y.; Rombouts, F. J. R.; Lubell, W. D. J. Comb. Chem. 2006, 8, 117.
40. (g) Chakraborty, T. K.; Udawant, S. P.; Roy, S.; Mohan, B. K.; Rao, K. S.; Dutta, S. K.; Kunwar, A. C. Tetrahedron Lett. 2006, 47, 4631. For examples of diamino pyrroles:
41. (h) Lyshchikov, A. N.; Pul'kherovskaya, O. V.; Vasil'ev, A. N.; Kayukov, Y. S.; Nasakin, O. E. Chem. Heterocycl. Compd. 2000, 36, 532.
42. (i) Attanasi, O. A.; De Crescentini, L.; Foresti, E.; Gatti, G.; Giorgi, R.; Perrulli, F. R.; Santeusanio, S. Perkin Trans 1 1997, 1829.
43. (j) Rehwald, M.; Schäfer, H.; Gewald, K. Monatsh. Chem. 1997, 128, 933.
44. (k) Abromovitch, R. A.; Cue, B. W.Jr. J. Am. Chem. Soc. 1976, 98, 1478.
45. (l) Abromovitch, R. A.;Cue,B. WJr. J. Org. Chem. 1973, 38, 173.
46. (m) Attanasi, O. A.; DeCrescentini, L.; Santeusanio, S.; Serra-Zanetti, F.; McKillop, A.; Liao, Z. Perkin Trans 1 1992, 1009.
47. CSD version 5.29, November 2007.
48. (a) Mason, M. R.; Fneich, B. N.; Kirschbaum, K. Inorg. Chem. 2003, 42, 6592.
49. (b) Mason, M. R.; Ogrin, D.; Fneich, B.; Barnard, T. S.; Kirschbaum, K. J. Organomet. Chem. 2005, 690, 157.
50. For related structurally characterized carbazole derivatives see: (a) Nygren, C. L.; Bragg, M. E. T.; Turner, J. F. C. Acta Crystallogr., Sect. C. Struct. Commun. 2003, 59, m275.
51. (b) Nygren, C. L.; Bragg, M. E. T.; Turner, J. F. C. Acta Crystallogr., Sect. C. Struct. Commun. 2004, 60, m4.
52. (c) Nygren, C. L.; Bragg, M. E. T.; Turner, J. F. C. Acta Crystallogr., Sect. C. Struct. Commun. 2004, 60, m94.
53. (d) Riley, P. N.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 1997, 1109.
54. (e) Riley, P. N.; Fanwick, P. E.; Rothwell, I. P. Dalton Trans. 2001, 181.
55. For other selected examples of titanium indolyl complexes see: (a) Zuo, W.; Sun, W.-H.; Zhang, S.; Hao, P.; Shiga, A. J. Polym. Sei A 2007,45,3415.
56. (b)Dias, A. R.;Dias,P. B.;Diogo,H.P.;Galvão, A.M.; Minas, M. E.; Simões, J. A. M. Organometallics 1987, 6, 1427.
57. (c) Calhorda, M. J.; Gomes, R.; Dias, A. R.; Simões, J. A. M. Dalton Trans. 1982, 2327.
58. (a) Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Chem. Commun. 2003, 586.
59. (b) Novak, A.; Blake, A. J.; Wilson, C.; Love, J. B. Chem. Commun. 2002, 23, 2796.
60. Majumder, S.; Gipson, K. R.; Staples, R. J.; Odom, A. L. Manuscript in preparation.
61. For these test reactions, phenylacetylene and 1-hexyne were used with aniline at 80 °C in toluene.
62. The double-isonitrile insertion into the Ti-C bond is favored over double insertion into the Ti-N bond of the azatitanacyclobutene because of the precedent for the former related to three-component coupling. In addition, three-component coupling products are often observed as minor products in the reactions of Table 1. However, double insertion into the Ti-N bond could lead to the same observed products. Single insertion into both sides of the azatitanacyclobutene would generate a formyl and amidinate at the two ends of the product; to generate thepyrrole, C-C bond formation would be required from these two groups, which seems unlikely.
63. Gokel, G. W.; Widera, R. P.; Weber, W. P. Org. Synth. 1976, 55, 96.
64. Bradley, D. C.; Thomas, I. M. Proc Chem. Soc. 1959, 225.