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1,3‐Dipolar cycloaddition reaction of 4,5‐dihydro‐1 H ‐imidazole 3‐oxides with alkynes
Author(s) -
Popov Sergey A.,
Chukanov Nikita V.,
Romanenko Galina V.,
Rybalova Tatjana V.,
Gatilov Yuri V.,
Reznikov Vladimir A.
Publication year - 2006
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.5570430206
Subject(s) - chemistry , imidazole , isoxazole , nitrone , cycloaddition , regioselectivity , medicinal chemistry , nitrogen atom , 1,3 dipolar cycloaddition , acceptor , nitrogen , ring (chemistry) , stereochemistry , catalysis , organic chemistry , physics , condensed matter physics
4,5‐Dihydro‐1 H ‐imidazole 3‐oxides bearing different substituents at positions 1 and 2 of the heterocycle were shown to react with a wide range of acceptor‐substituted alkynes forming corrsponding cycloadducts ‐ derivatives of 1,2,3,7a‐tetrahydroimidazo[1,2‐ b ]isoxazole. High regioselectivity of this process stipulated by conjugation of the nitrogen atom with the nitrone group was revealed.