Electrocyclization reactions of benzannulated 2-azaheptatrienyl- and 4-azanonatetraenyllithium compounds: Synthesis of N-acylated 2,3-dihydro-1H-benzo[c]azepines and a (5,6-dihydrobenzocycloocten-5-yl)amine

Synthesis

Volumn , Issue 13, 2006, Pages 2183-2190

  Sajitz, Melanie ^a   Fröhlich, Roland ^a   Salorinne, Kirsi ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Carbocycles; Heterocycles; Lithium; Quantum chemical calculations; Rearrangements; Ring closure

Indexed keywords

AROMATIZATION; HYDROGEN; LITHIUM; ORGANOMETALLICS; QUANTUM THEORY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBOCYCLES; HETEROCYCLES; QUANTUM CHEMICAL CALCULATIONS; REARRANGEMENTS; RING CLOSURE;

AROMATIC COMPOUNDS;

1 (3,4 DIPHENYL 2,3 DIHYDRO 1H BENZO[C]AZEPIN 2 YL) 2,2 DIMETHYLPROPAN 1 ONE; 1 [5 (2,2 DIMETHYLPROPRIONYL) 4 METHYL 3 VINYL 4,5 DIHYDRO 3H BENZO[C] AZEPIN 1 YL) 2,2 DIMETHYLPROPAN 1 ONE; 2 ACYL 2,3 DIHYDRO 1H BENZO[C]AZEPINE DERIVATIVE; 2 AZAHEPTATRIENYLLITHIUM; 2,2 DIMETHYL 1 (3 PHENYL 4 PROPYL 2,3 DIHYDRO 1H BENZO[C]AZEPIN 2 YL)PROPAN 1 ONE; 2,2 DIMETHYL 1 (4 METHYL 3 PHENYL 2,3 DIHYDRO 1H BENZO[C]AZEPIN 2 YL)PROPAN 1 ONE; 2,2 DIMETHYL 1 (4 METHYL 3 VINYL 2,3 DIHYDRO 1H BENZO[C]AZEPIN 2 YL)PROPAN 1 ONE; 2,2 DIMETHYL N (9 METHYL 5,6 DIHYDROBENZOCYCLOOCTEN 5 YL)PROPIONAMIDE; 4 AZANONATETRAENYLLITHIUM; ANNULENE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CHLORIDE; CHLOROFORM; CHLOROFORMIC ACID METHYL ESTER; IMINE; LITHIUM DERIVATIVE; METHYL 3 PHENYL 4 PROPYL 2,3 DIHYDRO 1H BENZO[C]AZEPINE 2 CARBOXYLATE; METHYL 4 METHYL 3 PHENYL 2,3 DIHYDRO 1H BENZO[C]AZEPINE 2 CARBOXYLATE; N ACYL (5,6 DIHYDROBENZOCYCLOOCTEN 5 YL)AMINE; N ACYL 2,3 DIHYDRO 1H BENZO[C]AZEPINE DERIVATIVE; PIVALOYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; PROTON TRANSPORT; QUANTUM CHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33746056434     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942414     Document Type: Article

References (28)

1. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed, Engl. 1969, 8, 781;
2. Angew. Chem. 1969, 81, 797.
3. Smalley, R. K. In Houben-Weyl, 4th ed., Vol. E 9d; Schaumann, E., Ed.; Thieme: Stuttgart, 1997, 207.
4. O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637.
5. Sternbach, L. H. J. Med. Chem. 1979, 22, 1.
6. Gerdes, K.; Sagar, P.; Fröhlich, R.; Wibbeling, B.; Würthwein, E.-U. Eur. J. Org. Chem. 2004, 3465.
7. Klötgen, S.; Würthwein, E.-U. Tetrahedron Lett. 1995, 36, 7085.
8. Klötgen, S.; Fröhlich, R.; Würthwein, E.-U. Tetrahedron 1996, 52, 14801.
9. Paquette, L. A. J. Am. Chem. Soc. 1964, 86, 4092.
10. Lennon, M.; McLean, A.; McWatt, I.; Proctor, G. R. J. Chem. Soc., Perkin Trans. 1 1974, 1828.
11. 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.; 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.
12. Grimme, S. J. Chem. Phys. 2003, 118, 9095.
13. (a) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763;
14. Angew. Chem. 1970, 82, 795.
15. (b) Vogel, C. Synthesis 1997, 497.
16. C-N Fission seems to be a common reaction step in the chemistry of unsaturated seven-membered aza heterocycles: Sagar, P.; Fröhlich, R.; Würthwein, E.-U. Angew. Chem. Int. Ed. 2004, 43, 5694;
17. Angew. Chem. 2004, 116, 5812.
18. Hibino, S.; Sugino, E.; Adachi, Y.; Nomi, K.; Sato, K.; Fukumoto, K. Heterocycles 1989, 28, 275.
19. Munro, D. P.; Sharp, J. T. J. Chem. Soc., Perkin Trans. 1 1984, 849.
20. Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron 1998, 54, 15525.
21. Hinterding, K.; Hagenbuch, P.; Retey, J.; Waldmann, H. Angew. Chem. Int. Ed. 1998, 37, 1236;
22. Angew. Chem. 1998, 110, 1298.
23. Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: (a) Data collection COLLECT: Nonius, B.V., 1998
24. (b) Data reduction Denzo-SMN: Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
25. (c) Absorption correction Denzo: Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr., Sect. A 2003, 59, 228.
26. (d) Structure solution SHELXS-97: Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
27. (e) Structure refinement SHELXL-97: Sheldrick, G. M., Universität Göttingen, 1997
28. (f) Graphics SCHAKAL: Keller, E., 1997. CCDC-603880 (7a), CCDC-603877 (7b), CCDC-603876 (7c), CCDC-606532 (7f), CCDC-603879 (9), CCDC-603878 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 IEZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].