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Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One‐Pot, Metal‐Free Heteroannulation to Functionalized 1,3‐Oxazoles
Author(s) -
Shah Shailesh R.,
Navathe Sudhanva S.,
Dikundwar Amol G.,
Guru Row Tayur N.,
Vasella Andrea T.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201269
Subject(s) - chemistry , oxazole , aryl , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , alkyl
α‐Azidoacetophenones were converted into 2‐aryl‐1,3‐oxazole‐4‐carbaldehydes through rearrangement of the carbon framework upon exposure to DMF/POCl 3 . The unprecedented rearrangement occurs via alkenyl azides and 2 H ‐azirines. A mechanism for this unusual reaction was proposed and evidenced.