REACTION OF BENZOCYCLOBUTENOXIDES WITH NITRILES - SYNTHESIS OF HYPECUMINE AND OTHER 3-SUBSTITUTED ISOQUINOLINES

Authors
FITZGERALD JJ MICHAEL FE OLOFSON RA
Citation
Jj. Fitzgerald et al., REACTION OF BENZOCYCLOBUTENOXIDES WITH NITRILES - SYNTHESIS OF HYPECUMINE AND OTHER 3-SUBSTITUTED ISOQUINOLINES, Tetrahedron letters, 35(49), 1994, pp. 9191-9194
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
49
Year of publication
1994
Pages
9191 - 9194
Database
ISI
SICI code
0040-4039(1994)35:49<9191:ROBWN->2.0.ZU;2-N
Abstract
Treatment of benzocyclobuten-2-ols with MeLi affords o-tolualdehyde an ions which in the presence of nitriles cyclize to 3-substituted isoqui nolines. Examples include the synthesis of the alkaloid hypecumine fro m the precursors, 14 and 19 (1:1), in 50% yield.