TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN3

Author:

He Yan1234,Xie Yu-yang1234,Wang Ying-chun5674,Bin Xiao-min1234,Hu Da-chao1234,Wang Heng-shan1234,Pan Ying-ming1234

Affiliation:

1. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources

2. School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University

3. Guilin 541004

4. People's Republic of China

5. College of Chemistry and Chemical Engineering

6. Jishou University

7. Jishou 416000

Abstract

A novel and efficient TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN3via the radical mechanism process is described. A plausible reaction mechanism for this process is proposed.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Reference59 articles.

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2. B. J. Wakefield , in Science of Synthesis: HoubenWeyl Methods of Molecular Transformations, ed. E. Schaumann, Georg Thieme Verlag, Stuttgart, New York, 2004, vol. 11, pp. 229–288

3. Recent Advances on the Synthesis and Reactivity of Isoxazoles

4. Synthesis and Biological Evaluation of Cyclopentaquinoline Derivatives as Nonsteroidal Glucocorticoid Receptor Antagonists

5. Structure–Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N′-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists

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