Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp®

C. J. Easton; G. A. Heath; C. M.M. Hughes; C. K.Y. Lee; G. P. Savage; G. W. Simpson; E. R.T. Tiekink; G. J. Vuckovic; R. D. Webster

doi:10.1039/b008081k

Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp®

C. J. Easton^*, G. A. Heath, C. M.M. Hughes, C. K.Y. Lee, G. P. Savage, G. W. Simpson, E. R.T. Tiekink, G. J. Vuckovic, R. D. Webster

^*Corresponding author for this work

Australian National University

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp®. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

Original language	English
Pages (from-to)	1168-1174
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	10
DOIs	https://doi.org/10.1039/b008081k
Publication status	Published - 2001
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry

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Easton, C. J., Heath, G. A., Hughes, C. M. M., Lee, C. K. Y., Savage, G. P., Simpson, G. W., Tiekink, E. R. T., Vuckovic, G. J., & Webster, R. D. (2001). Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp®. Journal of the Chemical Society, Perkin Transactions 1, (10), 1168-1174. https://doi.org/10.1039/b008081k

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title = "Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp{\textregistered}",

abstract = "Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp{\textregistered}. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.",

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language = "English",

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journal = "Journal of the Chemical Society, Perkin Transactions 1",

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AU - Easton, C. J.

AU - Heath, G. A.

AU - Hughes, C. M.M.

AU - Lee, C. K.Y.

AU - Savage, G. P.

AU - Simpson, G. W.

AU - Tiekink, E. R.T.

AU - Vuckovic, G. J.

AU - Webster, R. D.

PY - 2001

Y1 - 2001

N2 - Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp®. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

AB - Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp®. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

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Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp®

Abstract

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