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Synthesis of Heterocyclic Propellanes by 1,3‐Dipolar Cycloaddition of 2,6‐Dichlorobenzonitrile Oxide to 2,3‐Fused Indoles. Catalytic Hydrogenation of the Cycloadducts
Author(s) -
MalamidouXenikaki Elizabeth,
CoutouliArgyropoulou Evdoxia
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920115
Subject(s) - chemistry , indole test , catalysis , cycloaddition , catalytic hydrogenation , 1,3 dipolar cycloaddition , imine , oxide , organic chemistry , stereochemistry , medicinal chemistry
N ‐Methylcycloalkano[ b ]indoles 1a , 1c – d and N ‐methylindeno[1,2‐ b ]indole ( 1e ) react with 2,6‐dichlorobenzonitrile oxide ( 2 ) to afford regioselectively propellanes 3 . Catalytic hydrogenation of compounds 3 proceeds via the labile β‐hydroxyimines 4 , which are further decomposed to the starting indole and 2,6‐dichlorobenzonitrile. In one case the intermediate imine 4e is stable and isolated in pure form.