α-amination of nitrogen heterocycles: Ring-fused aminals

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 416-417

  Zhang, Chen ^a   De, Chandra Kanta ^a   Mal, Rudrajit ^a   Seidel, Daniel ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; NITROGEN; FUSED HETEROCYCLIC RINGS;

AMINATION; ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; FRIEDLANDER REACTION; HYDROGEN BOND; OXIDATION REDUCTION REACTION; SYNTHESIS; CHEMISTRY;

AMINATION; HETEROCYCLIC COMPOUNDS, 2-RING; NITROGEN;

EID: 40149096724     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077473r     Document Type: Article

References (35)

1. 3 C-H bonds adjacent to nitrogen in heterocycles, see: Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069-1084.
2. For examples of metal-catalyzed C-H bond aminations α to a heteroatom, see: (a) Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2007, 9, 3813-3816.
3. (b) Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784-11791.
4. For the formation of dihydrobenzimidazoles from ortho-dialkylaminoanilines using TMSCl as a promoter, see: Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Shivanyuk, A. N.; Tolmachev, A. A. J. Org. Chem. 2007, 72, 7417-7419.
5. Hiersemann, M. Functions bearing two nitrogens. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R. T., Richard J. K., Eds.; Elsevier Ltd.: Oxford, UK, 2005; Vol. 4, pp 411-441.
6. (a) Friedländer, P. Ber. 1882, 15, 2572-2575.
7. (b) Friedländer, P.; Gohring, C. F. Ber. 1883, 16, 1833-1839.
8. For recent mechanistic studies on the Friedländer reaction, see: Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461-478 and references cited therein.
9. The mechanistic hypothesis is related to reactions for which the "tert-amino effect" is invoked. For reviews, see: (a) Meth-Cohn, O.; Suschitzky, H. Adv. Heterocyel. Chem. 1972, 14, 211-278.
10. (b) Meth-Cohn, O. Adv. Heterocycl. Chem. 1996, 65, 1-37.
11. (c) Matyus, P.; Elias, O.; Tapolcsanyi, P.; Polonka-Balint, A.; Halasz-Dajka, B. Synthesis 2006, 2625-2639.
12. For an example of a reaction in which a 1,6-hydrogen transfer has been inferred, see: Reinhoudt, D. N.; Visser, G. W.; Verboom, W.; Benders, P. H.; Pennings, M. L. M. J. Am. Chem. Soc. 1983, 105, 4775-4781.
13. Transient dipoles have previously been generated by condensation of cyclic amines with α-dicarbonyl compounds followed by trapping through intra-or intermolecular dipolar cycloadditions: (a) Ardill, H.; Dorrity, M. J. R.; Grigg, R.; Leon-Ling, M. S.; Malone, J. F.; Sridharan, V.; Thianpatanagul, S. Tetrahedron 1990, 46, 6433-6448.
14. (b) Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167.
15. (c) Argyropoulos, N. G.; Sarli, V. C.; Gdaniec, M. Eur. J. Org. Chem. 2006, 3738-3745.
16. For the generation of dipolar intermediates from tetrahydroisoquinoline and aldehydes, see: (a) Ardill, H.; Fontaine, X. L. R.; Grigg, R.; Henderson, D.; Montgomery, J.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1990, 46, 6449-6466.
17. (b) Wang, B.; Mertes, M. P.; Mertes, K. B.; Takusagawa, F. Tetrahedron Lett. 1990, 31, 5543-5546.
18. Thus far, the scope seems to be limited to heterocyclic secondary amines. No reaction was observed with either methylbenzylamine or dibenzylamine.
19. (a) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765-2809.
20. (b) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517.
21. For selected examples of aminal-containing natural products, see: (a) Hino, T.; Nakagawa, M. Chemistry and reactions of cyclic tautomers of tryptamines and tryptophans. In Alkaloids; Academic Press: New York, 1988; Vol. 34, pp 1-75.
22. (b) Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151-161.
23. (c) Hajicek, J.; Taimr, J.; Budesinsky, M. Tetrahedron Lett. 1998, 39, 505-508.
24. (d) Braekman, J. C.; Daloze, D.; Pasteels, J. M.; Van Hecke, P.; Declercq, J. P.; Sinnwell, V.; Francke, W. Z. Naturforsch., C: Biosci. 1987, 42, 627-630.
25. For a review on quinazolinone alkaloids, see: Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787-9826.
26. Compounds such as 2k have been synthesized by reduction of quinazolinone alkaloids: Koretskaya, N. I.; Utkin, L. M. Zh. Obshch. Khim. 1958, 28, 1087-1089.
27. For selected examples of recent syntheses of deoxyvasicinone, see: (a) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2001, 66, 9038-9040.
28. (b) Liu, J.-F.; Ye, P.; Sprague, K.; Sargent, K.; Yohannes, D.; Baldino, C. M.; Wilson, C. J.; Ng, S.-C. Org. Lett. 2005, 7, 3363-3366.
29. (c) Lee, E. S.; Park, J.-G.; Jahng, Y. Tetrahedron Lett. 2003, 44, 1883-1886.
30. (d) Hamid, A.; Elomri, A.; Daich, A. Tetrahedron Lett. 2006, 47, 1777-1781.
31. (e) Bowman, W. R.; Elsegood, M. R. J.; Stein, T.; Weaver, G. W. Org. Biomol. Chem. 2007, 5, 103-113.
32. For selected examples of recent syntheses of rutaecarpine, see: (a) Mohanta, P. K.; Kim, K. Tetrahedron Lett. 2002, 43, 3993-3996.
33. (b) Mhaske, S. B.; Argade, N. P. Tetrahedron 2004, 60, 3417-3420.
34. (c) Harayama, T.; Hori, A.; Serban, G.; Morikami, Y.; Matsumoto, T.; Abe, H.; Takeuchi, Y. Tetrahedron 2004, 60, 10645-10649.
35. (d) Chavan, S. P.; Sivappa, R. Tetrahedron Lett. 2004, 45, 997-999 and also refs 15c-e.