Indole as neutral leaving group in silver nitrate induced cyclization reactions of n-{2-[alkynyl(hetero)aryl]methylene}indolin-1-amines for the synthesis of annulated pyridine derivatives

European Journal of Organic Chemistry

Volumn , Issue 9, 2010, Pages 1787-1797

  Ghavtadze, Nugzar ^a   Fröhlich, Roland ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Cyclization; Lewis acids; Nitrogen heterocycles; Quantum chemical calculations; Silver

Indexed keywords

EID: 77949278887     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901471     Document Type: Article

References (57)

1. M. B. Smith, J. March, in March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed., John Wiley & Sons, Inc., New York, 2001, pp. 815-820 and references wherein.
2. a) A. R. Katritzky, G. Musamarra, K. Sakizadeh, M. MisicVukovic, J. Org. Chem. 1981, 46, 3820-3823;
3. b) A. R. Katritzky, C. M. Marson, Angew. Chem. Int. Ed. Engl. 1984, 23, 420-429;
4. c) A. R. Katritzky, H. Schultz, M. L. Lopez-Rodriguez, J. Chem. Soc. Perkin Trans. 2 1987, 73-78;
5. d) A. R. Katritzky, B. E. Brycki, J. Phys. Org. Chem. 1988, 1, 1-20.
6. a) M. A. Ciufblini F. Roschangar, Tetrahedron 1997, 53, 11049-11060;
7. b) K. Matoba, K. Itoh, T. Yamazaki, M. Nagata, Chem. Pharm. Bull. 1981, 29, 2442-2450;
8. c) K. Matoba, Y. Miyata, T. Yamazaki, Chem. Pharm. Bull. 1983, 31, 476-481;
9. d) K. Matoba, T. Terada, M. Sugiuara, T. Yamazaki, Heterocycles 1987, 26, 55-58;
10. e) A. Aftfah, M. Y. Abu-Shuheil, J. Hill, Tetrahedron 1990, 46, 6483-6500;
11. f) D. A. Klumpp, Y. Zhang, M. J. O'Connor, P. M. Estevens, L. S. Almeida, Org. Lett. 2007, 9, 3085-3088;
12. g) J. Dieker, R. Froehlich, E.-U. Würthwein, Eur. J. Org. Chem. 2006, 5339 5356.
13. N. Ghavtadze, R. Fröhlich, E.-U. Würthwein, Eur. J. Org. Chem. 2008, 3656-3667,
14. highlighted in Synfacts 2008, 10, 1033-1033
15. a) K. R. Roesch, R. C. Larock, J. Org. Chem. 1998, 63, 5306-5307;
16. b) G. Dai, R. C. Larock, Org. Lett. 2001, 3, 4035-4038;
17. c) Q. Huang, J. A. Hunter, R. C. Larock, Org. Lett. 2001, 3, 2973-2976;
18. d) G. Dai, R. C. Larock, J. Org. Chem. 2002, 67, 7042-7047;
19. e) Q. Huang, R. C. Larock, Tetrahedron Lett. 2002, 43, 3557-3560;
20. f) Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437-3444;
21. g) K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86-94.
22. H. Gao, J. Zhang, Adv. Synth. Catal. 2009, 351, 85-88.
23. Y.-N. Niu, Z.-Y. Yan, G.-L. Gao, H.-L. Wang, X.-Z. Shu, K.G. Ji, Y.-M. Liang, J. Org. Chem. 2009, 74, 2893-2896.
24. a) D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil Y. Yamamoto, Angew. Chem. Int. Ed. 2007, 46, 4764-4766;
25. b) Z. Huo, H. Tomeba, Y. Yamamoto, Tetrahedron Lett. 2008, 49, 5531-5533;
26. c) D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc. 2008, 130, 15720-15725.
27. a) N. Asao, S. Yudha, S. T. Nogami, Y. Yamamoto, Angew. Chem. Int. Ed. 2005, 44, 5526-5528;
28. b) T. Sakamoto, Y. Kondo, N. Miura, K. Hayashi, H. Yamanaka, Heterocycles 1986, 24, 2311-2314;
29. c) A. Numata, Y. Kondo, T. Sakamoto, Synthesis 1999, 2, 306-311;
30. d) H.-S. Yeom, S. Kim, S. Shin, Synlett 2008, 6, 924-928;
31. e) Q. Ding, Z. Chen, X. Yu, Y. Peng, J. Wu, Tetrahedron Lett. 2009, 50, 340-342;
32. f) Z. Chen, X. Yang, J. Wu, Chem. Commun. 2009, 3469-3471.
33. [l0] N-Aminoindoline was prepared from commercially available indoline similar to the procedure described in: A. B. Smith III, L. Kürti, A. H. Davulcu, Org. Lett. 2006, 8, 2167-2170.
34. X-ray data sets were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326),
35. absorption correction SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 3337;
36. R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426)
37. and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr., Sect. A 2003, 59, 228-234),
38. structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473),
39. structure refinement SHELXL-97 (G. M. Sheldrick, Universität. Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-741418 (3a) and -741419 (41) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
40. a) Z. Huo, Y. Yamamoto, Tetrahedron Lett. 2009, 50, 36513653;
41. b) Y. Yamamoto, I. D. Gridnev, N. T. Patil, T. Jin, Chem. Commun. 2009, 5075-5087;
42. for the reviews, see: c) J. M. Weibel, A. Blanc, P. Pale, Chem. Rev. 2008, 108, 3149-3173;
43. d) M. Álvarez-Corral, M. Muñoz-Dorado, I. Rodriguez-Garcia, Chem. Rev. 2008, 108, 3174-3198;
44. e) N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442;
45. f) A. Arcadi, Chem. Rev. 2008, 108, 3266-3325.
46. G. Dai, R. C. Larock, J. Org. Chem. 2003, 68, 920-928.
47. a) M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Parkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Chaliacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford CT, 2004. Details of the quantum chemical calculations (Gaussian archive entries) may be obtained from E.-U. W. upon request. b) All computations in this study have been performed by using the Gaussian 03 suite of programs. The Becke three-parameter exchange functional and the correlation functional of Lee, Yang, and Parr (B3LYP) with the SDD basis set for the silver atom and 6-311G(d,p) basis set for the other atoms were used to compute the geometries and the normal-mode vibration frequencies of the starting cations, the corresponding transition structures, and the products. For single-point energy calculations on DFT-optimized geometries the SCS-MP2 method was used. The transition structure for the silver-catalyzed cyclization was localized by the option "opt = qst3", using the approximate geometries of the corresponding starting compound, transition state and product applying the B3LYP functional with the 6-311G(d,p)&SDD basis set. In order to verify the character of the stationary points, they were subjected to frequency analyses. In the text, E(0 K) energies are discussed, which contain zero-point corrections. The vibration related to the imaginary frequency corresponds to the nuclear motion along the reaction coordinate under study. An intrinsic reaction coordinate (IRC) calculation was performed in order to unambiguously connect the transition structure with the reactant and the product.
48. S. Grimme, J. Chem. Phys. 2003, 118, 9095-9102.
49. a) Y. Yamamoto, J. Org. Chem. 2007, 72, 7817-7831;
50. b) R. Gleiter, T. von Hirschheydt, F. Rominger, Eur. J. Inorg. Chem. 2000, 2127-2130;
51. c) R. Koschabek, R. Gleiter, F. Rominger, Eur. J. Inorg. Chem. 2006, 609-620;
52. d) H. V R. Dias, J. A. Flores, J. Wu, P. Kroll, J. Am. Chem. Soc. 2009, 131, 11249-11255.
53. For the synthesis of o-alkynylaldehydes, see: a) V. Lyaskovskyy, R. Fröhlich, E.-U. Würthwein, Chem. Eur. J. 2007, 13, 31133119;
54. b) V. Lyaskovskyy, K. Bergander, R. Fröhlich, E.-U. Würthwein, Org. Lett. 2007, 9, 1049-1052;
55. c) V. Lyaskovskyy, R. Fröhlich, E.-U. Würthwein, Synthesis 2007, 14, 2135-2144 and references wherein.
56. N-Aminoindoline was prepared from commercially available indoline similar to the procedure described in: A. B. Smith III, L. Kürti, A. H. Davulcu, Org. Lett. 2006, 8, 2167-2170.
57. C. K. Bradsher, T. G. Wallis, Tetrahedron Lett. 1972, 31, 31493150.