Formation and reaction of o-quinol acetates of N-acyl- and N- methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols

Heterocycles

Volumn 52, Issue 2, 2000, Pages 751-760

  Hoshino, Osamu ^a   Suzuki, Masaji ^a   Ogasawara, Hiromichi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; N METHANESULFONYL 1,2,3,4 TETRAHYDRO 6 METHOXYISOQUINOLIN 7 OL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HYDROGENATION; OXIDATION; REACTION ANALYSIS;

EID: 0034143288     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-S84     Document Type: Article

References (17)

1. O. Hoshino and B. Umezawa, "The Alkaloids", Ed. by A. Brossi, Vol. 36, Chapter 2, Academic Press, Inc., 1989 and references cited therein.
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5. On synthesis of optically active aporphine and morphinandienone alkaloids from p-quinol esters; see, H. Kara, S. Komoriya, T. Miyashita, and O. Hoshino, Tetrahedron: Asymmetry, 1995, 6, 1683.
6. S. M. Kupchan, O. P. Dhingta, and C-K. Kim, J. Org. Chem., 1978, 43, 4076.
7. a) O. Hoshino, M. Ohtani, and B. Umezawa, Chem. Pharm. Bull., 1979, 27, 3101.
8. b) O. Hoshino, M. Ohtani, B. Umezawa, and Y. Iitaka, Chem. Pharm. Bull., 1979, 32, 4873.
9. On o-QAs of four guaiacol-type tetrahydroisoquinolines; see, H. Hara, H. Shinoki, O. Hoshino, and B. Umezawa, Heterocycles, 1983, 20, 2149.
10. 2 at rt for 2 h gave 8d in 98% yield.
11. 2O-AcCl (100 °C); see, M. Mollow, S. Philipov, and H. Dutchewska, Chem. Ber., 1978, 111, 554.
12. 2O-AcCl (100 °C); see, M. Mollow, S. Philipov, and H. Dutchewska, Chem. Ber., 1978, 111, 554.
13. 2O-AcCl (100 °C); see, M. Mollow, S. Philipov, and H. Dutchewska, Chem. Ber., 1978, 111, 554.
14. 2O-AcCl (100 °C); see, M. Mollow, S. Philipov, and H. Dutchewska, Chem. Ber., 1978, 111, 554.
15. 2O-AcCl (100 °C); see, M. Mollow, S. Philipov, and H. Dutchewska, Chem. Ber., 1978, 111, 554.
16. Reaction of 2-hydroxy-N-methylaporphine and 2-hydroxy-N-cyanomethyl-N-methylaporphinium iodide to the corresponding phenanthrene derivatives under acidic conditions has been reported: With 80% aqueous propionic acid (reflux); see, S.-S. Lee, C.-M. Chiou, H.-Y. Lin, and C.-H. Chen, Tetrahedron Lett., 1995, 36, 6309: With conc. HCl-MeOH (reflux); see, H. Hara, K. Kaneko, M. Endoh, H. Uchida, and O. Hoshino, Tetrahedron, 1995, 51, 10189.
17. Reaction of 2-hydroxy-N-methylaporphine and 2-hydroxy-N-cyanomethyl-N-methylaporphinium iodide to the corresponding phenanthrene derivatives under acidic conditions has been reported: With 80% aqueous propionic acid (reflux); see, S.-S. Lee, C.-M. Chiou, H.-Y. Lin, and C.-H. Chen, Tetrahedron Lett., 1995, 36, 6309: With conc. HCl-MeOH (reflux); see, H. Hara, K. Kaneko, M. Endoh, H. Uchida, and O. Hoshino, Tetrahedron, 1995, 51, 10189.