Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives

Journal of Organic Chemistry

Volumn 74, Issue 12, 2009, Pages 4584-4591

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

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; CASCADE REACTIONS; CHEMICAL EQUATIONS; DOUBLE BONDS; ELECTROCYCLIZATION REACTIONS; GOOD YIELD; IMINIUM; PYRUVATES; QUANTUM CHEMICAL CALCULATIONS; RING SYSTEMS; TRANSITION STATE; TRIFLUOROMETHANE SULFONIC ACID; TRIFLUOROMETHYL;

ACIDS; AMINATION; AMINES; MOLYBDENUM; ORGANIC COMPOUNDS; QUANTUM CHEMISTRY; REACTION KINETICS;

CHEMICAL BONDS;

1',3' DIMETHYL 3 (TRIFLUOROMETHYL) 1',5' DIHYDROSPIRO(INDENE 1,4' PYRAZOLE); 2,4 DIMETHYL 6 (TRIFLUOROMETHYL) 2,3 DIHYDRO 1H INDENO[7,1,DE][1,2]DIAZEPINE; ALKADIENE; DIAZEPINE DERIVATIVE; ION; PYRAZOLE DERIVATIVE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; HORNER WADSWORTH EMMONS REACTION; QUANTUM CHEMISTRY; SOLVATION; SUBSTITUTION REACTION; X RAY DIFFRACTION;

EID: 67249157187     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900270e     Document Type: Article

References (63)

1. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. (b) Mueller, T. J. J.; D'Souza, D. M. Pure Appl. Chem. 2008, 80, 609.
3. (c) Tietze, L. F.; Modi, A. Med Res Rev. 2000, 20, 304-322.
4. (d) Enders, D.; Grondal, C.; Huetti, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
5. (e) Pellisier, H. Tetrahedron 2006, 62, 1619.
6. (f) Pellisier, H. Tetrahedron 2006, 62, 2143.
7. Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341.
8. (b) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967.
9. Schötz, K.; Clark, T.; Schleyer, P.v.R. J. Am. Chem. Soc. 1988, 110, 1394.
10. (a) Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049.
11. (b) Matoba, K.; Itoh, K.; Yamazaki, T.; Nagata, M. Chem. Pharm. Bull. 1981, 29, 2442.
12. (c) Matoba, K.; Miyata, Y.; Yamazaki, T. Chem. Pharm. Bull. 1983, 31, 476.
13. (d) Matoba, K.; Terada, T.; Sugiuara, M.; Yamazaki, T. Heterocycles 1987, 26, 55.
14. (e) Aftfah, A.; Abu-Shuheil, M. Y.; Hill, J. Tetrahedron 1990, 46, 6483.
15. (f) Klumpp, D. A.; Zhang, Y.; O'Connor, M. J.; Estevens, P. M.; Almeida, L. S. Org. Lett. 2007, 16, 3085.
16. (a) Dieker, J.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2006, 5339.
17. (b) Alickmann, D.; Fröhlich, R.; Maulitz, A. H.; Wurthwein, E.-U. Eur. J. Org. Chem. 2002, 1523.
18. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2008, 3656.
19. Neidlein, R.; Feistauer, H. Helv. Chim. Acta 1996, 79, 895.
20. Ghavtadze, N. Ph.D. thesis, University Münster, 2008.
21. Dhar, D. N.; Ragunathan, R. Tetrahedron 1984, 40, 1585.
22. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2009, 1228.
23. Ghavtadze, N.; Fröhlich, R.; Bergander, K.; Würthwein, E.-U. Synthesis 2008, 3397.
24. Data sets were collected with Enraf-Nonius CAD4 and Nonius KappaCCD diffractometers in the case of Mo radiation equipped with a rotating anode generator. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998), data reduction MolEN (Fair, K. Enraf-Nonius B.V., 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.)
25. Absorption correction for CCD-data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33.
26. Blessing, R. H. J. J. Appl. Crystallogr. 1997, 30, 421)
27. and Denzo (Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr. 2003, A59, 228.)
28. Structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.)
29. Structure refinement SHEXL-97 (Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.)
30. Graphics SCHAKAL (Keller, E. 1997). CCDC-693648 (6a), -693649 (3l), -693650 (5o), -693651 (4o), -693652 (6b), -693653 (6f), -693654 (6e) and-693655 (5e) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving. html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (int) +44(1223)336-1033, E-mail: deposit@ccdc.cam.ac.uk]
31. (a) Olah, G. A. Angew. Chem. 1993, 105, 805;
32. Angew. Chem., Int. Ed. Engl. 1993, 32, 767.
33. (b) Lammertsma, K.; Schleyer, P. v. R.; Schwarz, H. Angew. Chem. 1989, 101, 1313-1335;
34. Angew. Chem.; Int. Ed. Engl. 1989, 28, 1321.
35. (c) Olah, G. A.; Klumpp, D. A. Acc. Chem. Res. 2004, 37, 211.
36. (d) Olah, G. A.; Klumpp, D. A. Superelectrophiles and Their Chemistry; Wiley: New York, 2007.
37. (a) Snyder, J. P.; Heyman, M. L.; Gundestrup, M. J. Chem.Soc., Perkin Trans. 1 1977, 13, 1551.
38. (b) Wirschun, W. G.; Al-Soud, Y. A.; Nusser, K. A.; Orama, O.; Maier, G.-M.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 2000, 24, 4356.
39. (a) Kamitori, Y.; Hojo, M.; Masuda, R.; Ohara, S.; Kawasaki, K.; Yoshikawa, N. Tetrahedron Lett. 1988, 29 (41), 5281.
40. (b) Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokoyama, T. J. Org. Chem. 1988, 53, 129.
41. (c) Kamitori, Y.; Hojo, M.; Masuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519.
42. 19 The transition structure were further optimized at the DFT level with the Gaussian 03 package of programs using the option "mndofcquot; (opt ) (ts, noeigentest, mndofc)), applying the B3LYP/6-311G(d,p) basis set. In order to verify the character of the stationary points, they were subjected to frequency analyses. In the following 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. In significant cases intrinsic reaction coordinate (IRC) calculations were performed in order to unambiguously connect transition structures with reactants and products. Bond orders and atomic charges were calculated with the natural bond orbital (NBO) method as implemented in the Gaussian 03 program.
43. Gaussian 03: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; 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.; 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.; Pople, J. A. Gaussian 03, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2004. Details of the quantum chemical calculations (Gaussian archive entries) may be obtained from E.-U.W. upon request.
44. Grimme, S. J. Chem. Phys. 2003, 118, 9095.
45. (a) MOPAC2007: Stewart, J. J. P. Stewart Computational Chemistry, Colorado Springs, CO, 2007, http://OpenMOPAC.net.
46. (b) Stewart, J. J. P. J. Mol. Modeling 2007, 13, 1173.
47. (a) Kallel, E. A.; Houk, K. N. J. Org. Chem. 1989, 54, 6006.
48. (b) Smith, D. A.; Ulmer II, C. W. J. Org. Chem. 1997, 62, 5110.
49. (c) Faza, O. N.; Lopez, C. S.; Alvarez, R.; de Lera, A. R. Chem. - Eur. J. 2004, 10, 4324.
50. (a) Rzepa, H. S. J. Chem. Educ. 2007, 84, 1535.
51. (b) Jiao, H.; Schleyer, P.v.R. Angew. Chem. 1993, 105, 1833;
52. Angew. Chem., Int. Ed. 1993, 32, 1763.
53. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
54. (b) Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. V. R. Chem. Rev. 2005, 105, 3842.
55. (c) Stanger, A. J. Org. Chem. 2006, 71, 883.
56. (a) Heilbronner, E. Tetrahedron Lett. 1964, 1923.
57. (b) Zimmerman, H. E. J. Am. Chem. Soc. 1966, 88, 1564.
58. (c) Zimmerman, H. E. Acc. Chem. Res. 1971, 4, 272.
59. (d) Rzepa, H. S. Chem. Rev. 2005, 105, 3697.
60. (e) Herges, R. Chem. Rev. 2006, 106, 4820.
61. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. 1992, 104, 711;
62. Angew. Chem., Int. Ed. 1992, 31, 682.
63. For the nucleus in dependent chemical shift (NICS) calculations the gauge-independent atomic orbitals (GIAO) method using the 6-311+G(d,p) basis set on the B3LYP/6-311G(d,p) geometries was applied. NICS values were determined along an axis perpendicular to the center of the transition state structure (15 points above and below the plane of the forming ring system with a step width of 0.2 Å). The lowest value obtained is given in the text.