Medium-ring systems. 5. Synthesis and base-catalyzed isomerizations of medium-ring cycloalkenones with electron-withdrawing substituents

1984 ◽  
Vol 49 (16) ◽  
pp. 2925-2937 ◽  
Author(s):  
Ronnie C. Mease ◽  
Jerry A. Hirsch
Keyword(s):  
Ring Systems ◽  
Medium Ring ◽  
Electron Withdrawing Substituents

ChemInform Abstract: Cyclizations of Hydroxy Dithioketals. New Synthetic Technology for the Construction of Oxocenes and Related Medium-Ring Systems.

ChemInform ◽  
1989 ◽  
Vol 20 (43) ◽  
Author(s):  
K. C. NICOLAOU ◽  
C. V. C. PRASAD ◽  
C.-K. HWANG ◽  
M. E. DUGGAN ◽  
C. A. VEALE
Keyword(s):  
Ring Systems ◽  
Medium Ring

Synthesis of some 2,5-benzoxazocine and 2,6-benzoxazonine derivatives from ω-(Dihydroisoindol-2-yl)alkanol precursors by means of cyanogen bromide

1982 ◽  
Vol 35 (11) ◽  
pp. 2307 ◽  
Author(s):  
JB Bremner ◽  
N Thirasasana
Keyword(s):  
Cyanogen Bromide ◽  
Ring Systems ◽  
Derivatives Of ◽  
Medium Ring ◽  
Moderate Yield

Reaction of cyanogen bromide with 2-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)ethanol (5a) gave 1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine-5-carbonitrile (6a) in a low to moderate yield. Similarly, 3-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)propan-1-ol (5c) gave 1-phenyl-1,3,4,5,6,7-hexa-hydro-2,6-benzoxazonine-6-carbonitrile (6c). The analogous 1-(4-methoxyphenyl) derivatives of both medium ring systems were also prepared, and some mechanistic aspects of the results are discussed. Conversion of (6a) into the analgesic, Nefopam,is described.

Efficient Access to Functionalized Medium-Ring Systems by Radical Fragmentation/Radical Addition to α-Iodoketones.

ChemInform ◽  
2005 ◽  
Vol 36 (37) ◽  
Author(s):  
Corinne De Dobbeleer ◽  
Ali Ates ◽  
Jean-Christophe Vanherk ◽  
Istvan E. Marko
Keyword(s):  
Radical Addition ◽  
Ring Systems ◽  
Efficient Access ◽  
Radical Fragmentation ◽  
Medium Ring
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