Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One-Pot, Metal-Free Heteroannulation to Functionalized 1,3-Oxazoles

Shah, Shailesh R and Navathe, Sudhanva S and Dikundwar, Amol G and Row, Tayur Guru N and Vasella, Andrea T (2013) Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One-Pot, Metal-Free Heteroannulation to Functionalized 1,3-Oxazoles. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2). pp. 264-267.

PDF eur_jl_org_che_2_264_2013.pdf - Published Version Restricted to Registered users only Download (313kB) | Request a copy

Abstract

alpha-Azidoacetophenones were converted into 2-aryl-1,3-oxazole-4-carbaldehydes through rearrangement of the carbon framework upon exposure to DMF/POCl3. The unprecedented rearrangement occurs via alkenyl azides and 2H-azirines. A mechanism for this unusual reaction was proposed and evidenced.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copyright for this article belongs to the WILEY-V C H VERLAG GMBH, GERMANY.
Keywords:	Rearrangement; Oxygen heterocycles; Nitrogen heterocycles; Ketones
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	12 Apr 2013 11:16
Last Modified:	12 Apr 2013 11:16
URI:	http://eprints.iisc.ac.in/id/eprint/46408

Actions (login required)

View Item