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

Tetrahedron

Metal-free dual sp 3 C–H functionalization: I 2-promoted domino oxidative cyclization to construct 2, 5-disubstituted oxazoles

QH Gao, Z Fei, YP Zhu, M Lian, FC Jia, MC Liu, NF She…

Index: Gao, Qing-He; Fei, Zhuan; Zhu, Yan-Ping; Lian, Mi; Jia, Feng-Cheng; Liu, Mei-Cai; She, Neng-Fang; Wu, An-Xin Tetrahedron, 2013 , vol. 69, # 1 p. 22 - 28

Full Text: HTML

Citation Number: 48

Abstract

An I2-promoted sp3 C–H functionalization has been developed for the synthesis of 2, 5- disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C–H bond and the formation of C–N, C–O bonds.

4-Morpholinoacetophenone Structure

4-Morpholinoace...

~%

4-Morpholinophenylglyoxal hydrate Structure

4-Morpholinophe...

4-biphenylglyoxal hydrate Structure

4-biphenylglyox...

Benzylamine Structure

~%

5-[1,1'-biphenyl]-4-yl-2-phenyloxazole Structure

5-[1,1'-bipheny...

4-Acetylbiphenyl Structure

4-Acetylbiphenyl

~%

5-[1,1'-biphenyl]-4-yl-2-phenyloxazole Structure

5-[1,1'-bipheny...

2-iodo-1-phenylethanone Structure

2-iodo-1-phenyl...

Benzylamine Structure

~85%

2,5-Diphenyloxazole Structure

2,5-Diphenyloxazole

2,2-Dihydroxy-1-phenylethan-1-one Structure

2,2-Dihydroxy-1...

4-Fluorobenzylamine Structure

4-Fluorobenzylamine

~%

Oxazole,2-(4-fluorophenyl)-5-phenyl- Structure

Oxazole,2-(4-fl...

Phenylglyoxal Structure

~%

Oxazole,2-(4-fluorophenyl)-5-phenyl- Structure

Oxazole,2-(4-fl...

Acetophenone Structure

~%

Oxazole,2-(4-fluorophenyl)-5-phenyl- Structure

Oxazole,2-(4-fl...

2,2-Dihydroxy-1-phenylethan-1-one Structure

2,2-Dihydroxy-1...

(3-Chlorophenyl)methanamine Structure

(3-Chlorophenyl...

~%

Oxazole,2-(3-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(3-ch...

Phenylglyoxal Structure

~%

Oxazole,2-(3-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(3-ch...

Acetophenone Structure

~%

Oxazole,2-(3-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(3-ch...

2,2-Dihydroxy-1-phenylethan-1-one Structure

2,2-Dihydroxy-1...

4-Chlorobenzylamine Structure

4-Chlorobenzylamine

~%

Oxazole,2-(4-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(4-ch...

Phenylglyoxal Structure

~%

Oxazole,2-(4-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(4-ch...

Acetophenone Structure

~%

Oxazole,2-(4-chlorophenyl)-5-phenyl- Structure

Oxazole,2-(4-ch...

4-Methoxyphenylglyoxal hydrate Structure

4-Methoxyphenyl...

4-Methylbenzylamine Structure

4-Methylbenzylamine

~%

5-(4-methoxyphenyl)-2-(4-methylphenyl)-1,3-oxazole Structure

5-(4-methoxyphe...

Acetanisole Structure

~%

5-(4-methoxyphenyl)-2-(4-methylphenyl)-1,3-oxazole Structure

5-(4-methoxyphe...