Synthesis of 7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline: A key intermediate en route to makaluvamines, discorhabdin C and other marine alkaloids of this group via vicarious nucleophilic substitution of hydrogen

Synthesis

Volumn , Issue 10, 1997, Pages 1131-1133

  Ma̧kosza, Mieczysław ^a   Stalewski, Jacek ^a   Maslennikova, Olga S ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

Author keywords

Marine alkaloids precursor; Selective NO2 hydrogenation; Vicarious nucleophilic substitution

Indexed keywords

7,8 DIMETHOXY 2 OXO 1,3,4,5 TETRAHYDROPYRROLO[4,3,2 DE]QUINOLINE; ALKALOID; DISCORHABDIN C; MAKALUVAMINE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

EID: 0030835105     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1325     Document Type: Article

References (13)

1. Marki, F.; Robertson, A.V.; Witkop, B. J. Am. Chem. Soc. 1961, 83, 3341.
2. Roberts, D.; Alvarez, M.; Joule, J.A. Tetrahedron Lett. 1996, 37, 1509 and references cited therein.
3. (a) Tao, X.L.; Cheng, J.-F.; Nishiyama, S.; Yamamura, S. Tetrahedron 1994, 50, 2017.
4. (b) Izawa, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 917;
5. Tetrahedron 1994, 48, 13593.
6. Ma̧kosza, M.; Stalewski, J. Tetrahedron 1995, 51, 7263.
7. Yamada, F.; Hamabuchi, S.; Shimizu, A.; Somei, M. Heterocycles 1995, 41, 1905.
8. Ma̧kosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20, 272;
9. Ma̧kosza, M. Synthesis 1991, 103.
10. Ma̧kosza, M.; Ludwiczak, S. J. Org. Chem. 1984, 49, 4562.
11. Theodoridis, G.; Manfredi, M.C.; Krebs, J.D. Tetrahedron Lett. 1990, 31, 6141.
12. Grochowski, E.; Eckstein, Z. Bull. Acad. Sci., Ser. Chim. 1963, 11, 443.
13. Borsche, W. Chem. Ber. 1917, 50, 1347.