Bischler-napieralski cyclization-N/C-alkylation sequences for the construction of isoquinoline alkaloids. Synthesis of protoberberines and benzo[c]phenanthridines via C -2′-functionalized 3-arylisoquinolines

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4062-4072

  Sotomayor, Nuria ^a   Domínguez, Esther ^a   Lete, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BENZO[C]PHENANTHRIDINE DERIVATIVE; PROTOBERBERINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029893856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960007s     Document Type: Article

References (71)

1. For preliminary communications: Sotomayor, N.; Domínguez, E.; Lete, E. Synlett 1993, 431. Sotomayor, N.; Domínguez, E.; Lete, E. Tetrahedron Lett. 1994, 35, 2973.
2. For preliminary communications: Sotomayor, N.; Domínguez, E.; Lete, E. Synlett 1993, 431. Sotomayor, N.; Domínguez, E.; Lete, E. Tetrahedron Lett. 1994, 35, 2973.
3. Simánek, V.: Benzophenanthridine Alkaloids. In The Alkaloids. Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press, Inc.: Orlando, 1985; Vol. 26; p 229.
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9. (a) For a review on benzo[c]phenanthridine synthesis, see ref 2, p 209.
10. (b) For a review on protoberberine synthesis, see ref 3, p 134.
11. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
12. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
13. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
14. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
15. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
16. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
17. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
18. For a few representative examples, see the following. Protoberberine synthesis from (a) 1-benzylisoquinolines: Suau, R.; Valpuesta, M. Tetrahedron 1990, 46, 4421. (b) N-Phenethyl-1,4-dihydroisoquinolinium salts: Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115; J. Org. Chem. 1978, 43, 4183. (c) N-acylalkylidenetetrahydroisoquinolines: Naito, T.; Katsumi, K.; Toda, Y.; Ninumiya, I. Heterocycles 1983, 20, 775. Lenz, G. R. J. Org. Chem. 1977 42, 1117. (d) N-functionalized 3-arylisoquinolines: Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. Benzolclphenanthridine synthesis from (e) 4-phenylacetylisoquinolones: Onda, M.; Harigaya, Y.; Suzuki, T. Chem. Pharm. Bull. 1977, 23B, 79. (f) C-4-functionalized isoquinolines: Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc., Chem. Commun. 1970, 1797. (g) C-4-functionalized isoquinolones: Cushman, M; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
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