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

Hao-Yang Wang; Yuan-Xi Liao; Yin-Long Guo; Qing-Hong Tang; Long Lu

doi:10.1055/s-2005-865235

LETTER

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

Hao-Yang Wang^a,b, Yuan-Xi Liao^a, Yin-Long Guo*^a, Qing-Hong Tang^b, 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;

Abstract

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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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Referenzen

References

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6

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

7 Wang H.-Y. Guo Y.-L. Lu L. J. Am. Soc. Mass Spectrom. 2004, 15: 1820

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8a Kleb KG. Angew. Chem., Int. Ed. Engl. 1968, 7: 291

8b Selvakumar N. Srinivas D. Azhagan AM. Synthesis 2002, 2421

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9a Rodig OR. Collier RE. Schlatzer RK. J. Org. Chem. 1964, 29: 2652

9b Shin JM. Cho YM. Sachs G. J. Am. Chem. Soc. 2004, 126: 7800