Tetrahedron

Unusual Rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2, 5-disubstituted Oxazoles

AD Clark, WK Janowski, RH Prager

Index: Clark, Adrian D.; Janowski, Wit K.; Prager, Rolf H. Tetrahedron, 1999 , vol. 55, # 12 p. 3637 - 3648

Full Text: HTML

Citation Number: 11

Abstract

Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5 (2H)-ones leads to good yields of 2- aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5-phenyloxazoles and 5-aryl-2- phenyloxazoles. The mechanism of formation of the 2, 5-disubstituted products has been investigated by 13C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.

Related Articles:

Total synthesis of dimethyl sulfomycinamate

[Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633]

A novel improved procedure for the synthesis of oxazoles

[Huang, Wei; Pei, Jian; Chen, Bingzi; Pei, Weiwei; Ye, Xiulin Tetrahedron, 1996 , vol. 52, # 30 p. 10131 - 10136]

A domino copper-catalyzed CN and CO cross-coupling for the conversion of primary amides into oxazoles

[Schuh, Kerstin; Glorius, Frank Synthesis, 2007 , # 15 p. 2297 - 2306]

Total synthesis of dimethyl sulfomycinamate

[Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633]

Total synthesis of dimethyl sulfomycinamate

[Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633]

More Articles...