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Synthesis 2016; 48(01): 65-72
DOI: 10.1055/s-0035-1560492
DOI: 10.1055/s-0035-1560492
paper
A Convenient Synthesis of Spiro[isoxazole-pyrazoloquinoline] Derivatives under Catalyst-Free Conditions
Further Information
Publication History
Received: 03 August 2015
Accepted after revision: 14 September 2015
Publication Date:
19 October 2015 (online)
Abstract
The same three-component reaction of aromatic aldehyde, 1H-indazol-6-amine and 3-phenylisoxazol-5(4H)-one in refluxing ethanol under catalyst-free conditions gave two entirely different kinds of products depending on the substituents on the benzene ring. The reaction selectively gave 5H-spiro[isoxazole-4,8′-pyrazolo[3,4-f]quinolin]-5-ones with strong electron-withdrawing groups on the aromatic aldehyde, while it resulted in ring-opened pyrazoloquinoline derivatives with other substituents. The former structure was confirmed by X-ray diffraction analysis.
Key words
pyrazoloquinolines - ring opening - 1H-indazol-6-amines - 3-phenylisoxazol-5(4H)-ones - catalyst freeSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560492.
- Supporting Information
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