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Synlett 2005(8): 1239-1242  
DOI: 10.1055/s-2005-865235
LETTER
© Georg Thieme Verlag Stuttgart · New York

Interesting Acid-Catalyzed O-N-Type Smiles Rearrangement Reactions of 2-Pyrimidinyloxy-N-Arylbenzylamine Derivatives

Hao-Yang Wanga,b, Yuan-Xi Liaoa, Yin-Long Guo*a, Qing-Hong Tangb, Long Lu*b
a Shanghai Mass Spectrometry Center, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: 86(21)64166128; e-Mail: ylguo@mail.sioc.ac.cn; e-Mail: lulong@mail.sioc.ac.cn;
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Publication History

Received 10 March 2005
Publication Date:
21 April 2005 (online)

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Abstract

The acid-catalyzed O-N-type Smiles rearrangement reactions of 2-pyrimidinyloxy-N-arylbenzylamine derivatives were investigated. The results show most 2-pyrimidinyloxy-N-aryl­benzylamine derivatives can also undergo the Smiles rearrangement to the corresponding phenol derivatives in good yields at 25 °C in acetic acid-acetone (1:1).

Key words

Smiles rearrangement - acidic conditions - 2-pyrimidinyloxy-N-arylbenzylamine

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Analytical data for these compounds are available upon request from the authors. Compounds 1a and 1c have been used in rape fields in China.