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Beckmann rearrangement; cyclization; & #x03B2; -oximyl amides; oxazolines; triflic anhydride.

Facile and efficient synthesis of 5-iminooxazolines fromΑ, Α-disubstituted Β-oximyl amidesmediated by triflic anhydride $(Tf_{2}O)$ in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) indichloromethane at room temperature is developed, and a mechanism involving tandem Beckmann rearrangementand intramolecular cyclization reaction is proposed.

MANGFEI YU¹ QIAN ZHANG² JIA WANG² PENG HUANG² PENGFEI YAN¹ RUI ZHANG² DEWEN DONG²

1. School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, China
2. Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

Published

8 June 2016

Manuscript received

19 January 2016

Manuscript revised

14 March 2016

Accepted

27 March 2016

• JCSC_128_6_951_956_SI.docx