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Rearrangements of substituted 3‐azidoazetidines: Unexpected formation of a substituted oxazole
Author(s) -
Marchand Alan P.,
Rajagopal D.,
Bott Simon G.
Publication year - 1995
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.5570320453
Subject(s) - chemistry , yield (engineering) , acetonitrile , microcrystalline , oxazole , titanium tetrachloride , imine , sodium azide , solvent , thermal decomposition , medicinal chemistry , dichloromethane , organic chemistry , titanium , crystallography , catalysis , materials science , metallurgy
Thermolysis of neat N ‐carboethoxy‐3‐azido‐3‐ethylazetidine ( 3 ) at 200° under argon produced the corresponding cyclic imine 4 (68% yield). Prolonged refluxing of a mixture of N ‐triflylazetidin‐3‐one ( 7 ), sodium azide, and titanium tetrachloride in acetonitrile solvent afforded recovered 7 (25% yield) along with a colorless microcrystalline solid, 8 , mp 104–105° (20% yield), whose structure was established unequivocally via application of X‐ray crystallographic methods.