Diastereoselective synthesis of linear-fused tricyclic nitrogen heterocycles by a tandem reduction-reductive amination reaction

Journal of Heterocyclic Chemistry

Volumn 40, Issue 1, 2003, Pages 101-106

  Bunce, Richard A ^a   Herron, Derrick M ^a   Lewis, Jason R ^a   Kotturi, Sharadsrikar V ^a   Holt, Elizabeth M ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; ANILINE DERIVATIVE; ANTIDEPRESSANT AGENT; ESTER; HETEROCYCLIC COMPOUND; HYDROXYLAMINE; IMINE; NITROGEN DERIVATIVE; TRICYCLIC AROMATIC COMPOUND;

ALKYLATION; AMINATION; ARTICLE; CIS TRANS ISOMERISM; CYCLIZATION; DRUG SYNTHESIS; HYDROGENATION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037288178     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400113     Document Type: Article

References (33)

1. Undergraduate Research Participants: D. M. H., 1999-present; J. R. L., 2001-2002.
2. [b] Author to whom questions regarding the X-ray crystal structures should be addressed. E-mail: betsy@biochem.okstate.edu
3. R. A., Bunce, D. M. Herron, L. B. Johnson and S. V. Kotturi, J. Org. Chem., 66, 2822 (2001).
4. V. G. Ermolaeva, V. G. Yashunskii, A. I. Polezhaeva and M. D. Mashkovskii, Khim.-Farm. Zh., 2, 20 (1968); Chem. Abstr., 69, 106517 (1968).
5. V. G. Ermolaeva, V. G. Yashunskii, A. I. Polezhaeva and M. D. Mashkovskii, Khim.-Farm. Zh., 2, 20 (1968); Chem. Abstr., 69, 106517 (1968).
6. D. J. Collins, P. F. Drygala and J. M. Swan, Aust. J. Chem., 36, 2095 (1983).
7. A. Barco, S., Benetti and G. P. Pollini, Synthesis, 316 (1973).
8. D. A. Jeyaraj, K. K. Kapoor, V. K. Yadav, H. M. Grauniyal and M. Parvez, J. Org. Chem., 63, 287 (1998). For the preparation of potassium fluoride-on-alumina see, V. K. Yadav and K. K. Kapoor, Tetrahedron, 52, 3659 (1996).
9. D. A. Jeyaraj, K. K. Kapoor, V. K. Yadav, H. M. Grauniyal and M. Parvez, J. Org. Chem., 63, 287 (1998). For the preparation of potassium fluoride-on-alumina see, V. K. Yadav and K. K. Kapoor, Tetrahedron, 52, 3659 (1996).
10. D. Henderson, K. A. Richardson, R. J. K. Taylor and J. Saunders, Synthesis, 996 (1983).
11. E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, NY, 1994, pp 774-777;
12. [b] T. A. Crabb, in Cyclic Organonitrogen Stereodynamics, J. B. Lambert and Y. Takeuchi, Eds., VCH, New York, NY, 1992, pp 253-287.
13. A. E. Derome, Modern NMR Techniques for Chemistry Research, Elsevier Science, New York, NY, 1987, pp 227-230;
14. [b] T. D. W. Claridge, High-Resolution NMR Techniques in Organic Chemistry; Elsevier Science, New York, NY, 1999, pp 158, 188, 197-199.
15. D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, NY, 1989, pp 253-306.
16. 3, 2021 observed reflections (F° > 2.0(σF)). This crystal, and several others of this compound, diffracted poorly. Refinement of nonhydrogen positional and anisotropic thermal parameters along with positional parameters for hydrogen atoms (using idealized geometry) refined to only 12.9%, but clearly showed the cis ring junction.
17. W. H. Perkins Jr. and W. G. Sedgwick, J. Chem. Soc., 125, 2437 (1924);
18. [b] H. Adkins and H. L. Coonradt, J. Am. Chem. Soc., 63, 1563 (1941);
19. [c] E. Hayashi and T. Nagao, Yakugaku Zasshi, 84, 198 (1964); Chem Abstr., 63, 3071 (1964);
20. [c] E. Hayashi and T. Nagao, Yakugaku Zasshi, 84, 198 (1964); Chem Abstr., 63, 3071 (1964);
21. [d] I. Mochida, M. Ohira, K. Sakanishi, H. Fujitsu and H. Okazaki, Nippon Kagaku Kaishi, 1033 (1987); Chem Abstr., 108, 112189y (1988);
22. [d] I. Mochida, M. Ohira, K. Sakanishi, H. Fujitsu and H. Okazaki, Nippon Kagaku Kaishi, 1033 (1987); Chem Abstr., 108, 112189y (1988);
23. [e] K. Sakanishi, M. Ohira, I. Mochida, H. Okazaki and M. Soeda, J. Chem. Soc., Perkin Trans. 2, 1769 (1988);
24. [f] S. E. Booth, P. R. Jenkins and C. J. Swain, J. Chem. Soc., Chem. Commun., 147 (1993).
25. These compounds were also synthesized in ref 12a by reduction of 1,2,3,4-tetrahydroacridine with tin and hydrochloric acid, but no product ratio was given. In a latter paper, the cis and trans assignments were unclear, see W. H. Perkin Jr. and W. G. Sedgwick, J. Chem. Soc., 438 (1926). Compare melting points with J. Buckingham, Ed., Dictionary of Organic Compounds, Vol 4, 5th Ed., Chapman and Hall, New York, NY, 1982, p 4368, entry 0-00284.
26. These compounds were also synthesized in ref 12a by reduction of 1,2,3,4-tetrahydroacridine with tin and hydrochloric acid, but no product ratio was given. In a latter paper, the cis and trans assignments were unclear, see W. H. Perkin Jr. and W. G. Sedgwick, J. Chem. Soc., 438 (1926). Compare melting points with J. Buckingham, Ed., Dictionary of Organic Compounds, Vol 4, 5th Ed., Chapman and Hall, New York, NY, 1982, p 4368, entry 0-00284.
27. These conditions are more commonly used for the reduction of pyridines and involve reduction of the N-formylated heterocycle with formic acid followed by deformylation with concentrated hydrochloric acid. See [a] R. Lukes and J. Pliml, Collect. Czech. Chem. Commun., 15, 463 (1950); [b] M. Hudlicky, Reductions in Organic Chemistry, 2nd Ed., ACS, Washington, DC, 1996, pp 47 and 71.
28. These conditions are more commonly used for the reduction of pyridines and involve reduction of the N-formylated heterocycle with formic acid followed by deformylation with concentrated hydrochloric acid. See [a] R. Lukes and J. Pliml, Collect. Czech. Chem. Commun., 15, 463 (1950); [b] M. Hudlicky, Reductions in Organic Chemistry, 2nd Ed., ACS, Washington, DC, 1996, pp 47 and 71.
29. R. A. Bunce, D. M. Herron, J. R. Lewis and S. V. Kotturi, J. Heterocyclic Chem., 40, 113 (2003). In this study, control experiments indicated that either the hydroxylamine or the aniline could be intermediates in the reaction.
30. W. C. Stille, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).
31. XSCANS Users Manual; Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA (1991).
32. G. M. Sheldrick, Acta Cryst., A46, 467 (1990).
33. G. M. Sheldrick, SHELXL97 Program for the Refinement of Crystal Structures, University of Gottingen, Germany (1997).