A domino cyclization reaction of iminium salts: A convenient route to hexahydrobenzo[b]phenanthrolines

Synlett

Volumn , Issue 3, 2006, Pages 391-394

  Kiselyov, Alexander S ^a  

^a CHEMDIV INC   (United States)

Author keywords

Domino cyclizations; Hexahydrobenzo b phenanthroline; Iminium salts

Indexed keywords

ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; HEXAHYDROBENZO[B]PHENANTHROLINE DERIVATIVE; PHENANTHROLINE DERIVATIVE; PRENYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33344454308     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926236     Document Type: Article

References (43)

1. (a) Grieco, P.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855.
2. (b) Kiselyov, A. S.; Armstrong, R. W. Tetrahedron Lett. 1997, 38, 6163.
3. (a) Campos, P. J.; Lamaza, I.; Rodriguez, M. A.; Canal, G. Tetrahedron Lett. 1997, 38, 6741.
4. (b) Clerici, A.; Porta, O. Tetrahedron Lett. 1990, 31, 2069.
5. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
6. (d) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656.
7. (e) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251.
8. (f) Nomura, Y.; Kimura, M.; Takeuchi, S.; Tomoda, S. Chem. Lett. 1978, 267.
9. (g) Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1997, 53, 9715.
10. For the general reviews on hetero Diels-Alder reactions, see: (a) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087.
11. (b) Boger, D. L. Tetrahedron 1983, 39, 2869.
12. See also: (c) Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
13. (d) Waldmann, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 274.
14. (e) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
15. (f) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990.
16. (g) Oppolzer, W. In Comprehensive Organic Synthesis, Vol. 5; Paquette, L. A., Ed.; Pergamon: Oxford, 1991, 315.
17. (h) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
18. (i) Waldmann, H. Synthesis 1994, 535.
19. (j) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
20. (a) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
21. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977.
22. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1095.
23. (d) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
24. (e) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
25. For synthesis of tetrahydroquinolines and their biological activity see for example: Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031; and references cited therein.
26. (a) Kiselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089.
27. (b) Kiselyov, A. S.; Smith, L. S.; Virgilio, A.; Armstrong, R. W. Tetrahedron 1998, 54, 7987.
28. (a) Schulte, J. L.; Laschat, S.; Kotila, S.; Hecht, J.; Fröhlich, R.; Wibbeling, B. Heterocycles 1996, 43, 2713.
29. (b) Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856.
30. (c) Twin, H.; Batey, R. A. Org. Lett. 2004, 6, 4913.
31. (d) Powell, D. A.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7569.
32. (e) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913.
33. (a) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493.
34. (b) Gowravaram, S.; Venkata, R. E.; Narjis, F.; Yadav, J. S.; Rama Krishna, K. V. S.; Kunwar, A. C. Synthesis 2004, 1150.
35. (c) Gowravaram, S.; Reddy, E. V.; Yadav, J. S.; Rama Krishna, K. V. S.; Sankar, A. R. Tetrahedron Lett. 2002, 43, 4029.
36. Zhang, D.; Kiselyov, A. S. Synlett 2001, 1173.
37. 2Br, -78°C to r.t., 2 h; iii) DIBAL-H, THF, 0°C, 1 h.
38. 2O (start: 20:80; finish 60:40 ratio; 15 min run; 0.05% of formic acid added) with a flow rate of 20 mL/min.
39. 3) or temperature (boiling in xylenes or chlorobenzene in the presence of p-TsOH or camphorsulphonic acid) were not successful. This result may be attributed to the unfavorable. (Diagram presented). Scheme 4 thermodynamics for the formation of this [5,5] fused system. Notably, the attempted reactions of the 2-pyridyl aldehyde derivatives with a single or no Me substituent at the double bond failed as well, presumably due to the insufficient electron density on the olefinic fragment. Similar difficulties in the intramolecular cycloaddition reactions for the formation of fused have been reported, see for example: (a) Wu, H.-J.; Lin, S.-H.; Lin, C.-C. Heterocycles 1994, 38, 1507.
40. (b) Cattal, M.; Cossu, S.; Fabris, F.; DeLucci, O. Synth. Commun. 1996, 26, 637.
41. (c) Burrell, S. J.; Derome, A. E.; Edenborough, M. S.; Harwood, L. M.; Leeming, S. A.; Isaacs, N. S. Tetrahedron Lett. 1985, 26, 2229.
42. 2: C, 76.57; H, 6.78; N, 9.92. Found: C, 76.36; H, 6.63; N, 9.77.
43. Observed relevant NOE (Figure 1; shifts of the bridge protons are indicated in ppm). (Diagram presented).