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Issue 24, 2011
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An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones

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Abstract

An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones has been developed using intramolecular 1,3-dipolar cycloaddition. The hydrazonoyl chloride, the precursor of the cycloadduct, is accessed easily through a two-step reaction carried out in one-pot. It is then used without purification for the base induced formation of the nitrilimine, which undergoes subsequent in situ intramolecular cycloaddition with an alkyne to afford the desired product. The reaction protocol has also been applied in bis-heteroannulation and in the synthesis of uracil derivatives of biological interest. The operational simplicity of the process, the use of cheap starting materials, and the relatively short reaction times required make the process convenient and practical.

Graphical abstract: An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones

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Supplementary files

Article information


Submitted
09 Aug 2011
Accepted
06 Sep 2011
First published
06 Sep 2011

Org. Biomol. Chem., 2011,9, 8422-8429
Article type
Paper

An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones

K. Brahma, A. K. Sasmal and C. Chowdhury, Org. Biomol. Chem., 2011, 9, 8422
DOI: 10.1039/C1OB06353G

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