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RESEARCH ARTICLE
Contents Vol 64(5)

Novel Synthesis of 2-thienylcarbonyl-cyclohexane-1,3-dione as Building Block for Indazolones and Isoxazolones

Guillermo M. Chans A , Elizabeth L. Moyano A B and Gloria I. Yranzo A
+ Author Affiliations
- Author Affiliations

A INFIQC – Department of Organic Chemistry, Faculty of Chemical Sciences, National University of Córdoba, Córdoba, Argentina.

B Corresponding author. Email: lauramoy@fcq.unc.edu.ar

Australian Journal of Chemistry 64(5) 638-646 https://doi.org/10.1071/CH11015
Submitted: 7 January 2011  Accepted: 14 February 2011   Published: 30 May 2011

Abstract

A new synthetic methodology using ultrasonic treatment was applied to the C-acylation of 1,3-cyclohexanedione with thiophene-2-carbonyl chloride to afford 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one (5). This compound was used as a building block to prepare different bicyclic systems: tetrahydro-4H-indazol-4-ones (7a–c and 9a,b,d), and 6,7-dihydrobenzisoxazole (11) by reaction with different hydrazines and hydroxylamine, respectively. Structural elucidation of all compounds was thoroughly achieved by NMR spectroscopy.


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