A convenient and versatile route to hydroquinolines by inter- and intramolecular Aza-Diels-Alder pathways

Angewandte Chemie - International Edition

Volumn 38, Issue 13-14, 1999, Pages 1928-1931

  Steinhagen, Henning ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Antiviral agents; Azaxylylenes; Cycloadditions; Heterocycles; Stereocontrol

Indexed keywords

AMIDE; HETEROCYCLIC COMPOUND; HYDROCHLORIC ACID; QUINOLINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033549497     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990712)38:13/14<1928::aid-anie1928>3.0.co;2-1     Document Type: Article

References (19)

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4. Y. Ito, S. Miyata, M. Nakatsuka, T. Saegusa, J. Am. Chem. Soc. 1981, 103, 5250-5251.
5. a) R. D. Bowen, D. E. Davies, C. W. G. Fishwick, T. O. Glasbey, S. J. Noyce, R. C. Storr, Tetrahedron Lett. 1982, 23, 4501-4504;
6. b) J. M. Wiebe, A. S. Caillé, L. Trimble, C. K. Lau, Tetrahedron 1996, 52, 11705-11724; see also
7. c) E. Foresti, P. Spagnolo, P. Zanirato, J. Chem. Soc. Perkin Trans. 1, 1989, 1354-1356.
8. For a general review of Diels-Alder additions with other types of azadienes, see L. Tietze in Top. Curr. Chem. 1997, 189, 1-120.
9. The substrates 1a-1c of Scheme 1 were prepared from o-aminobenzyl alcohol by the sequence: 1) N-acylation or N-sulfonylation, and 2) conversion of the resulting benzyl alcohol into the corresponding chloride by reaction with thionyl chloride in dichloromethane.
10. 1 [I > 2σ(I)] = 0.0386;
11. 1 [I > 2σ(I)] = 0.0481;
12. 1 [I > 2σ(I)] = 0.0601. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-113239/113240/ 113241. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
13. S. Ōmura, A. Nakagawa, Tetrahedron Lett. 1981, 22, 2199-2202.
14. a) M. L. Hill, R. A. Raphael, Tetrahedron 1990, 46, 4587-4594;
15. b) Y. Morimoto, H. Shirahama, Tetrahedron 1996, 52, 10609-10630.
16. R[(-)-8] = 30.0 min.
17. The substrates 3, 5, and 7 were prepared starting from the corresponding allylic alcohols by the sequence: 1) conversion into chloroformates by reaction with phosgene, 2) treatment of the chloroformates with o-aminobenzyl alcohol, and 3) conversion of the resulting hydroxy carbamates into the corresponding chlorides with thionyl chloride (see experimental section for details). 3-Chloro-2-methyl-2-propen-1-ol was prepared according to A. Mooradian, J. B. Cloke, J Am. Chem. Soc. 1946, 68, 785-789; L. F. Hatch, J. J. Russ, L. B. Gordon, J. Am. Chem. Soc. 1947, 69, 2614-2616. Enantiomerically pure (R)-2-cyclohexen-1-ol was prepared by kinetic resolution with lipase as described by T. Fukazawa, T. Hashimoto, Tetrahedron: Asymmetry 1993, 4, 2323-2326.
18. The substrates 3, 5, and 7 were prepared starting from the corresponding allylic alcohols by the sequence: 1) conversion into chloroformates by reaction with phosgene, 2) treatment of the chloroformates with o-aminobenzyl alcohol, and 3) conversion of the resulting hydroxy carbamates into the corresponding chlorides with thionyl chloride (see experimental section for details). 3-Chloro-2-methyl-2-propen-1-ol was prepared according to A. Mooradian, J. B. Cloke, J Am. Chem. Soc. 1946, 68, 785-789; L. F. Hatch, J. J. Russ, L. B. Gordon, J. Am. Chem. Soc. 1947, 69, 2614-2616. Enantiomerically pure (R)-2-cyclohexen-1-ol was prepared by kinetic resolution with lipase as described by T. Fukazawa, T. Hashimoto, Tetrahedron: Asymmetry 1993, 4, 2323-2326.
19. The substrates 3, 5, and 7 were prepared starting from the corresponding allylic alcohols by the sequence: 1) conversion into chloroformates by reaction with phosgene, 2) treatment of the chloroformates with o-aminobenzyl alcohol, and 3) conversion of the resulting hydroxy carbamates into the corresponding chlorides with thionyl chloride (see experimental section for details). 3-Chloro-2-methyl-2-propen-1-ol was prepared according to A. Mooradian, J. B. Cloke, J Am. Chem. Soc. 1946, 68, 785-789; L. F. Hatch, J. J. Russ, L. B. Gordon, J. Am. Chem. Soc. 1947, 69, 2614-2616. Enantiomerically pure (R)-2-cyclohexen-1-ol was prepared by kinetic resolution with lipase as described by T. Fukazawa, T. Hashimoto, Tetrahedron: Asymmetry 1993, 4, 2323-2326.