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1,3‐Dipolar cycloaddition reactions of 1‐methyl‐ and 1,3‐dimethylindol‐2‐yl nitrile oxides
Author(s) -
MalamidouXenikaki E.,
Stampelos X. N.,
CoutouliArgyropoulou E.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330305
Subject(s) - nitrile , chemistry , cycloaddition , oxide , 1,3 dipolar cycloaddition , organic chemistry , medicinal chemistry , catalysis
Reactions of the in situ prepared 1‐methylindol‐2‐yl nitrile oxide ( 2a ) with dipolarophiles lead to isoxazolines 5 and isoxazoles 8 and to their chloro‐derivatives 6 and 9 in good yields. Analogous reactions of the 1,3‐dimethylindol‐2‐yl nitrile oxide ( 2b ) give the isoxazolines 10 and the isoxazoles 12 as main products as well as their oxidation products 11 and 13 in low yields. The mechanism of the reactions and the spectral elucidation of the cycloadducts are discussed.