e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

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

SR Shah, SS Navathe, AG Dikundwar…

Index: Shah, Shailesh R.; Navathe, Sudhanva S.; Dikundwar, Amol G.; Guru Row, Tayur N.; Vasella, Andrea T. European Journal of Organic Chemistry, 2013 , # 2 p. 264 - 267

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Citation Number: 2

Abstract

Abstract 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 2H-azirines. A mechanism for this unusual reaction was proposed and evidenced.

2-Azido-1-(4-chlorophenyl)ethanone Structure

2-Azido-1-(4-ch...

~%

2-(4-Chlorophenyl)Oxazole-4-Carbaldehyde Structure

2-(4-Chlorophen...

4-Chlorobenzoic acid Structure

4-Chlorobenzoic acid

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

2-(4-Chlorophenyl)Oxazole-4-Carbaldehyde Structure

2-(4-Chlorophen...

4-Chlorobenzoic acid Structure

4-Chlorobenzoic acid

2-azido-1-phenylethanone Structure

2-azido-1-pheny...

~%

2-Phenyl-1,3-oxazole-4-carbaldehyde Structure

2-Phenyl-1,3-ox...

benzoic acid Structure

2-Bromoacetophenone Structure

2-Bromoacetophenone

~%

2-Phenyl-1,3-oxazole-4-carbaldehyde Structure

2-Phenyl-1,3-ox...

benzoic acid Structure

2-azido-1-phenylethanone Structure

2-azido-1-pheny...

~%

2-Phenyl-1,3-oxazole-4-carbaldehyde Structure

2-Phenyl-1,3-ox...

benzoic acid Structure

2-Bromoacetophenone Structure

2-Bromoacetophenone

~%

2-Phenyl-1,3-oxazole-4-carbaldehyde Structure

2-Phenyl-1,3-ox...

benzoic acid Structure

2-azido-1-(4-methylphenyl)ethanone Structure

2-azido-1-(4-me...

~%

2-P-TOLYL-OXAZOLE-4-CARBALDEHYDE Structure

2-P-TOLYL-OXAZO...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~%

2-P-TOLYL-OXAZOLE-4-CARBALDEHYDE Structure

2-P-TOLYL-OXAZO...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

2-azido-1-(4-bromophenyl)ethanone Structure

2-azido-1-(4-br...

~%

2-(4-Bromophenyl)-1,3-oxazole-4-carbaldehyde Structure

2-(4-Bromopheny...

4-Bromobenzoic acid Structure

4-Bromobenzoic acid

2-azido-1-(4-methoxyphenyl)ethanone Structure

2-azido-1-(4-me...

~%

2-(4-Methoxyphenyl)-1,3-oxazole-4-carbaldehyde Structure

2-(4-Methoxyphe...

p-Anisic acid Structure

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2-(4-Methoxyphenyl)-1,3-oxazole-4-carbaldehyde Structure

2-(4-Methoxyphe...

p-Anisic acid Structure