Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2361-2364

  Ishikawa, Teruhiko ^a   Manabe, Shinobu ^a   Aikawa, Toshiaki ^a   Kudo, Takayuki ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; QUINOLINE DERIVATIVE;

ACIDITY; ALKALINITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; ISOMERIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 3242706211     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049301u     Document Type: Article

References (24)

1. Skraup, Z. H. Ber. 1880, 13, 2086-2087.
2. Several modifications based on the Skraup method (ref 1) are well-known as Doebner-von Miller, Combes, Conrad-Limpach, and Friedländer quinoline synthesis; for these, see: Gilchrust, T. L. Heterocyclic Chemistry, 3rd ed.; Addison-Wesley Longman: Essex, 1997; pp 158-164.
3. For the most recent paper concerned with Friedländer synthesis employing o-nitrobenzaldehydes as a starting material, see: McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257-4259.
4. (a) Mayr, H.; Bäuml, E. Tetrahedron Lett. 1983, 24, 357-360.
5. (b) Mayr, H.; Bäuml, E. Tetrahedron Lett. 1984, 25, 1127-1130.
6. (c) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214.
7. (d) Müller, T. J. J.; Nets, A. Organometallics 1998, 17, 3609-3614.
8. (e) Olah, G. A.; Krishnamurti, R.; Parakash, G. K. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 1.8.
9. (a) Ishikawa, T.; Okano, M.; Aikawa, T.; Saito, S. J. Org. Chem. 2001, 66, 4635-4642.
10. (b) Ishikawa, T.; Aikawa, T.; Mori, Y.; Saito, S. Org. Lett. 2002, 5, 51-54.
11. For ruthenium-catalyzed propargylation of aromatic compounds, see: (a) Nishibayashi, Y.; Yoshikawa, M.; Inaba, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846-11847. (b) Hishibayashi, Y.; Inaba, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 7900-7901.
12. For ruthenium-catalyzed propargylation of aromatic compounds, see: (a) Nishibayashi, Y.; Yoshikawa, M.; Inaba, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846-11847. (b) Hishibayashi, Y.; Inaba, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 7900-7901.
13. For isomerization of this class, see: Reinhard, R.; Glaser, M.; Neumann, R.; Maas, G. J. Org. Chem. 1997, 62, 7744-7751.
14. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679-680.
15. Series of reactions shown in Scheme 3 led to 1a-h in 40-50% overall yields from the corresponding aniline or its derivatives. This method was unsuccessful for bromo or nitro derivatives.
16. 2, whereas most of Friedel-Crafts reactions required a stoichiometric amount of Lewis acid: see ref 4e.
17. Benzophenone bearing appropriate substituents on the rings should be examined in this context, which, however, has not been done yet.
18. Most previous reports for the synthesis of 1-benzazepine backbone from aniline derivatives featured the formation of a seven-membered heterocyclic ring relying on a functional group incorporated into an ortho substituent of the aniline derivatives: see, for example: (a) Zheng, Z. B.; Dowd, P. Tetrahedron Lett. 1993, 34, 7709-7712. (b) Anastasiou, D.; Jackson, W. R. Austr. J. Chem. 1992, 45, 21-37. (c) Sato, T.; Ito, T.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull. 1990, 38, 3331-3334. On the other hand, to the best of our knowledge, there has been no report with respect to the formation of 1-benzazocine derivatives featuring an IMFC process for heterocyclic ring closure employing aniline derivatives as a starting material.
19. Most previous reports for the synthesis of 1-benzazepine backbone from aniline derivatives featured the formation of a seven-membered heterocyclic ring relying on a functional group incorporated into an ortho substituent of the aniline derivatives: see, for example: (a) Zheng, Z. B.; Dowd, P. Tetrahedron Lett. 1993, 34, 7709-7712. (b) Anastasiou, D.; Jackson, W. R. Austr. J. Chem. 1992, 45, 21-37. (c) Sato, T.; Ito, T.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull. 1990, 38, 3331-3334. On the other hand, to the best of our knowledge, there has been no report with respect to the formation of 1-benzazocine derivatives featuring an IMFC process for heterocyclic ring closure employing aniline derivatives as a starting material.
20. Most previous reports for the synthesis of 1-benzazepine backbone from aniline derivatives featured the formation of a seven-membered heterocyclic ring relying on a functional group incorporated into an ortho substituent of the aniline derivatives: see, for example: (a) Zheng, Z. B.; Dowd, P. Tetrahedron Lett. 1993, 34, 7709-7712. (b) Anastasiou, D.; Jackson, W. R. Austr. J. Chem. 1992, 45, 21-37. (c) Sato, T.; Ito, T.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull. 1990, 38, 3331-3334. On the other hand, to the best of our knowledge, there has been no report with respect to the formation of 1-benzazocine derivatives featuring an IMFC process for heterocyclic ring closure employing aniline derivatives as a starting material.
21. In this case, unsaturated ketone was obtained probably through the Meyer-Schuster rearrangement due to a small amount of water inevitably present in the reaction medium. Hence, prolonged reaction did not lead to an increase in the yield of 12.
22. 2.
23. Series of reactions shown in Scheme 6 led to 13a-d in 40-50% overall yields from the corresponding benzyl halides.
24. No identifiable product was obtained. This probably means that the side chain was subject to decomposition due to the slow rate of the IFCR process in these cases.