Unprecedented hydrothermal reaction of o-phenylaniline and related derivatives with cyclic ketones. A novel approach to the construction of phenanthridine and quinoline ring systems

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1605-1608

  Mehta, Barun K ^a   Yanagisawa, Kazumichi ^a   Shiro, Motoo ^b   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PHENANTHRIDINE DERIVATIVE; PHENYLALANINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE; THERMAL EXPOSURE; X RAY CRYSTALLOGRAPHY;

EID: 0141629392     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0300120     Document Type: Article

References (25)

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4. Thermal Electrocyclic Reactions; Marvell, E. N.; Academic Press: New York, 1980.
5. For a related work on the synthesis of phenanthridines from o-phenylanilines via radical cyclization, see: Leardini, R.; Tundo, A.; Zanardi, G. Synthesis 1985, 107.
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11. For reviews see: Siskin, M.; Katritzky, A. R. Science 1991, 254, 231. Katritzky, A. R.; Allin, S. M.; Siskin, M. Acc. Chem. Res. 1996, 29, 399. Bröll, D.; Kaul, C.; Krämer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998. Savage, P. E. Chem. Rev. 1999, 99, 603. Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
12. For reviews see: Siskin, M.; Katritzky, A. R. Science 1991, 254, 231. Katritzky, A. R.; Allin, S. M.; Siskin, M. Acc. Chem. Res. 1996, 29, 399. Bröll, D.; Kaul, C.; Krämer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998. Savage, P. E. Chem. Rev. 1999, 99, 603. Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
13. For reviews see: Siskin, M.; Katritzky, A. R. Science 1991, 254, 231. Katritzky, A. R.; Allin, S. M.; Siskin, M. Acc. Chem. Res. 1996, 29, 399. Bröll, D.; Kaul, C.; Krämer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998. Savage, P. E. Chem. Rev. 1999, 99, 603. Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
14. For reviews see: Siskin, M.; Katritzky, A. R. Science 1991, 254, 231. Katritzky, A. R.; Allin, S. M.; Siskin, M. Acc. Chem. Res. 1996, 29, 399. Bröll, D.; Kaul, C.; Krämer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998. Savage, P. E. Chem. Rev. 1999, 99, 603. Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
15. 3) δ 14.03, 22.58, 26.16, 26.91 (x2), 29.48, 32.13, 34.67 (x2), 36.20, 44.94, 119.23, 122.41, 123.40, 125.15, 126.35, 126.98, 128.13, 129.10, 130.09, 132.99, 142.04, 146.21, 161.54.
16. We found that the product ratio was highly dependent upon the molar concentration of 1a: at 0.04 M, 3a (72%) and 3b (12%) (Table 1, entry 1); at 0.07 M, 3a (54%) and 3b (16%); at 0.1 M, 3a (46%) and 3b (23%); at 0.2 M, 3a (40%) and 3b (40%); and at 0.4 M, 3a (32%) and 3b (42%).
17. There is only one precedent for this type of cycloalkylation of anilines: Gataullin, R. R.; Kazhanova, T. V.; Fatykhov, A. A.; Spirikhin, L. V.; Abdrakhmanov, I. B. Russ. Chem. Bull. 2000, 49, 174. Mechanistic studies on this unusual reaction are currently in progress and will be reported in the future.
18. In a separate reaction, we confirmed that no detectable amount of 3b was formed by the treatment of 3a with 2a under the same conditions.
19. Compound 3f could only be detected by GCMS analysis of the crude sample.
20. 3) δ 23.90, 25.95, 34.42, 38.33, 120.42, 122.16, 123.81, 126.16, 126.59, 128.52, 128.97, 129.23, 129.95, 134.38, 143.07, 143.18, 163.69.
21. See Supporting Information.
22. Berson, J. A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, pp 311-390. Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. In Small Ring Compounds in Organic Synthesis I; de Meijere, A., Ed.; Springer-Verlag: Berlin, 1986; pp 138-141.
23. Berson, J. A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, pp 311-390. Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. In Small Ring Compounds in Organic Synthesis I; de Meijere, A., Ed.; Springer-Verlag: Berlin, 1986; pp 138-141.
24. In this case 2,4-dimethylquinoline was also detected as a minor byproduct (5% yield). This might be formed by condensation of 1b with acetone, formed by decomposition of 1b (see Scheme 3), followed by electrocyclization and aromatization.
25. Similar reactions using acyclic ketones such as 3-pentanone and benzophenone gave only a complex mixture of products.