Rearrangements of substituted 3‐azidoazetidines: Unexpected formation of a substituted oxazole | Zendy

Marchand Alan P. | Zendy; Rajagopal D. | Zendy; Bott Simon G. | Zendy

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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.

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