LEWIS-ACID-DIRECTED REACTIONS OF BENZOQUINONE MONOIMINES BISIMINES - APPLICATION TO SYNTHESES OF SUBSTITUTED BETA-TETRAHYDROCARBOLINES AND GAMMA-TETRAHYDROCARBOLINES/

Authors
ENGLER TA WANNER J
Citation
Ta. Engler et J. Wanner, LEWIS-ACID-DIRECTED REACTIONS OF BENZOQUINONE MONOIMINES BISIMINES - APPLICATION TO SYNTHESES OF SUBSTITUTED BETA-TETRAHYDROCARBOLINES AND GAMMA-TETRAHYDROCARBOLINES/, Tetrahedron letters, 38(35), 1997, pp. 6135-6138
Citations number
56
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
35
Year of publication
1997
Pages
6135 - 6138
Database
ISI
SICI code
0040-4039(1997)38:35<6135:LROBMB>2.0.ZU;2-M
Abstract
Ti(IV)-promoted reactions of N-phenylsulfonyl-3- and 4-piperidone enol ethers with -alkoxy-4-(N-phenylsulfonyl)imino-1,4-benzoquinone afford 8-alkoxy-7-hydroxy-tetrahydrocarbolines. However, reactions promoted by BF3 produce substituted benzofurans. Ti(IV)- or BF3-promoted reacti ons of -(N-benzoyl)-4-(N-phenylsulfonyl)-1,4-benzoquinone bisimines al so afford substituted tetrahydrocarboline derivatives. (C) 1997 Elsevi er Science Ltd.