Regioselective synthesis of heterocycles containing nitrogen neighboring an aromatic ring by reductive ring expansion using diisobutylaluminum hydride and studies on the reaction mechanism

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 627-636

  Cho, Hidetsura ^a   Iwama, Yusuke ^a   Sugimoto, Kenji ^a   Mori, Seiji ^b   Tokuyama, Hidetoshi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; BASIS SETS; CATION INTERMEDIATES; CHEMICAL EQUATIONS; DIISOBUTYLALUMINUM HYDRIDE; ELECTRON-RICH; HETEROCYCLES; INTRINSIC REACTION COORDINATE; KETOXIMES; POTENTIAL ENERGY CURVES; REACTION MECHANISM; REGIOSELECTIVE SYNTHESIS; RING EXPANSION; RING-EXPANSION REACTION; SADDLE POINT; SECONDARY AMINES; SYSTEMATIC INVESTIGATIONS; TRANSITION STATE;

AROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY; POTENTIAL ENERGY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

REACTION INTERMEDIATES;

1,2,3,4,5,6 HEXAHYDROAZEPIN[3,2 B]INDOLE; 1,2,3,4,5,6 HEXAHYDROBENZ[B]AZOCINE; 2,3,4,5 TETRAHYDRO 1H BENZOTHIEN[2,3 B]AZEPINE; 2,3,4,5 TETRAHYDRO 1H BENZOTHIEN[3,2B]AZEPINE; 2,3,4,5 TETRAHYDROBENZO[B][1,4]THIAZEPINE; 3,4 DIHYDRO 2H BENZ[B][1,4]OXAZINE; 5,6 DIHYDROPHENANTHRIDINE; 5,6,11,12 TETRAHYDRODIBENZ[B, F]AZOCINE; ALUMINUM; AZEPINE DERIVATIVE; AZOCINE DERIVATIVE; DIISOBUTYLALUMINUM HYDRIDE; INDOLE DERIVATIVE; NITROGEN; OXAZINE DERIVATIVE; PHENANTHRIDINE DERIVATIVE; THIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; REACTION ANALYSIS; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITROGEN OXIDES; ORGANOMETALLIC COMPOUNDS; OXIMES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 75749128224     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902177p     Document Type: Article

References (56)

1. Danaruma, L. G.; Heldt, W. E. Org. React. 1960, 11, 1-156.
2. (a) Cho, H.; Murakami, K.; Nakanishi, H.; Isoshima, H.; Hayakawa, K.; Uchida, I. Heterocycles 1998, 48, 919-927.
3. (b) Cho, H.; Matsuki, S. Heterocycles 1996, 43, 127-131.
4. Aparajithan, K.; Thompson,A. C.; Sam, J. J. Heterocycl. Chem. 1966, 3, 466-469.
5. Wolff, H. Org. React. 1946, 307-336.
6. Kunick, C. Arch. Pharm. (Weinheim) 1991, 324, 579-581.
7. (a) Cho, H.; Murakami, K.; Nakanishi, H.; Fujisawa, A.; Isoshima, H.; Niwa, M.; Hayakawa, K.; Hase, Y.; Uchida, I.; Watanabe, H.; Wakitani, K.; Aisaka, K. J. Med. Chem. 2004, 47, 101-109.
8. (b) Cho, H.; Wakitani, K. Japan Patent Application, H7-291540 (Nov 9, 1995), WO97/17349.
9. (c) Cho, H.; Murakami, K.; Fujisawa, A.; Niwa, M.; Nakanishi, H.; Uchida, I. Heterocycles 1998, 48, 1555-1566.
10. (a) Hattori, K,; Matsumura, Y; Miyazaki, T.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 7368-7370.
11. (b) Sasatani, S.; Miyazaki, T.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4711-4712.
12. (c) Fujiwara, J.; Sano, H.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1984, 25, 2367-2370.
13. Torisawa, Y.; Nishi, T.; Minamikawa, J. Bioorg. Med. Chem. Lett. 2002, 12, 387-390.
14. Willand, N.; Beghyn, T.; Nowogrocki, G.; Gesquiere, J.-C.; Deprez, B. Tetrahedron Lett. 2004, 45, 1051-1054.
15. Ortiz-Marciales, M.; Rivera, L. D.; Jesús, M. D.; Espinosa, S.; Benjamin, J. A.; Casanova, O. E.; Figueroa, I. G.; Rodríguez, S.; Correa, W. J. Org. Chem. 2005, 70, 10132-10134.
16. Mukhopadhyay, P. P.; Miyata, O.; Naito, T. Synlett 2007, 1403-1406.
17. Cho, H.; Iwama, Y.; Sugimoto, K.; Kwon, E.; Tokuyama, H. Heterocycles 2009, 78, 1183-1190.
18. The spectral data of oximes 5a, 5b, 5c, 5d, 5e, 5f, and 5m are identical with those reported previously.
19. (a) For 5a, see: Bubb, W. A.; Sternhell, S. Aust. J. Chem. 1976, 29, 1685-1697.
20. (b) For 5b and 5c, see: Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett. 2008, 10, 505-507.
21. (c) For 5d, see: Bonvallet, P. A.; Todd, E. M.; Kim, Y. S.; McMahon, R. J. J. Org. Chem. 2002, 67, 9031-9042.
22. (d) For 5e and 5f, see: Clive, D. L. J.; Pham, M. P.; Subedi, R. J. Am. Chem. Soc. 2007, 129, 2713-2717.
23. (e) For 5i, see: Bascop, S.-I.; Laronze, J.-Y.; Sapi, J. Monatsh. Chem. 1999, 130, 1159-1166.
24. (f) For 5m, see: Jain, N.; Kumar, A.; Chauhan, S. M. S. Tetrahedron Lett. 2005, 46, 2599-2602.
25. The precursor ketones of 5b, 5c, 5d, 5f, 5h, 5k, and 5n are commercially available. Precursor ketones of 5a, 5e, 5g, and 5i were prepared according to procedures in the literature.
26. (a) For the precursor ketone of 5a, see: Bubb, W. A.; Sternhell, S. Aust. J. Chem. 1976, 29, 1685-1697.
27. (b) For the precursor ketone of 5e, see: Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333-4339.
28. (c) For the precursor ketone of 5g, see: Mukherjee, C.; Kamila, S.; De, A. Tetrahedron 2003, 59, 4767-4774.
29. (d) For the precursor ketone of 5i, see: Li, X; Vince, R. Bioorg. Med. Chem. 2006, 14, 2942-2955.
30. (e) For cyclization from the carboxylic acid to the precursor ketone of 5j, see: Cho, H.; Matsuki, S. Heterocycles 1996, 43,127-131.
31. Maertens, F.; Toppet, S.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2005, 61, 1715-1722.
32. (f) For new synthesis of the precursor ketone of 5k, see Scheme S1 shown in the Supporting Information. (As for the starting material, 2-iodobenzo[b]thiophene, consult ref S1 in the Supporting Information.)
33. (g) For the precursor ketone of 5l, see: Horaguchi, T.;Kubo, T.; Tanemura, K.; Suzuki, T. J. Heterocyclic. Chem. 1998, 35, 649-653.
34. Ahlbrecht, H.; Düber, E. O.; Epsztajn, J.; Marcinkowski, R. M. K. Tetrahedron 1984, 40, 1157-1165.
35. Torraca, K. E.; Kawabe, S.-I.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12907-12908.
36. Mukheerjee, C.; Biehl, E. Heterocycles 2004, 63, 2309-2318.
37. Hirata, K.; Ogawa, N.; Sinagawa, Y.; Kiguchi, T.; Inoue, T.; Komeda, Y.; Yamashita, I.; Kamiya, Y. Application WO 2007139002, WO 2007-JP60678, Priority: JP 2006-147261, US 2006-809966. Hirata et. al. synthesized the human URAT-1 inhibitor in several steps by using compound 6e obtained from the reaction of 2H-1,4-benzoxazin-3(4H)-one with sodium bis(2-methoxyethoxy)aluminum hydride in toluene at rt.
38. Barluenga, J.; Fañanás, F. J.; Sanz, R.; Fernández, Y. Chem.;Eur. J. 2002, 8, 2034-2046.
39. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley: New York, 1986. References cited therein.
40. Cances, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
41. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
42. The spectral data of oximes 5o, 5w, 5x, 5y, and 5z are identical with those reported previously. (a) For 5o, 5x, and 5y, see: Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett. 2008, 10, 505-507.
43. (b) For 5w, see: Hwu, J. R.; Tseng, W. N.; Patel, H. V.; Wong, F. F.; Horng, D.-N.; Liaw, B. R.; Lin, L. C. J. Org. Chem. 1999, 64, 2211-2218.
44. (c) For 5z, see: Liu, S.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2007, 9, 1947-1950.
45. The spectral data of amines 6o, 6v, 6w, 6x, and 6y are identical with those reported previously. (a) For 6o, see: Ventrice, T.; Campi., E. M.; Roy Jackson, W.; Patti, A. F. Tetrahedron 2001, 57, 7557-7574.
46. (b) For 6v, 6w, 6x, and 6y, see: Byun, E.; Hong, B.; De Castro,K. A.; Lim, M.; Rhee, H. J. Org. Chem. 2007, 72, 9815-9817.
47. As to determination of the chemical structure of the products, the 1H NMR data of 6q and 6s were respectively identified with those of the compounds synthesized by reductive amination of (p-trifluoromethyl)- benzaldehyde with p-anisidine or aniline, followed by NaBH4 (Supporting Information, Scheme S2).
48. Sydnes, M. O.; Kuse, M.; Isobe, M. Tetrahedron 2008, 64, 6406-6414.
49. Harmata, M.; Zheng, P.; Huang, C.; Gomes, M. G.; Ying, W.; Ranyanil, K.-O.; Balan, G.; Calkins, N. L. J. Org. Chem. 2007, 72, 683-685.
50. (a) For an example of using DIBALH in process chemistry, see: Hobson, L. A.; Nugent, W. A.; Anderson, S. R.; Deshmukh, S. S.; Haley, J. J. III; Liu, P.; Magnus, N. A.; Sheeran, P.; Sherbine, J. P.; Stone, B. R. P.; Zhu, J. Org. Process Res. Dev. 2007, 11, 985-995.
51. (b) In the case of cyclohexanone oxime, large-scale production using DIBALH is also underway at a chemical corporation.
52. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, revision D.02; Gaussian Inc.: Wallingford, CT, 2004.
53. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368.
54. (c) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
55. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
56. Nicolas, Y; Blanchard, P.; Levillain, E.; Allain, M.; Mercier, N.; Roncali, J. Org. Lett. 2004, 6, 273-276.