3+2 -cycloadditions of 2-aminothioisomunchnones to alkynes: Synthetic scope and mechanistic insights


Arevalo, M. J., Avalos, M., Babiano, R., Cintas, P., Hursthouse, M. B., Jimenez, J. L., Light, M. E., Lopez, I. and Palacios, J. C. (2000) 3+2 -cycloadditions of 2-aminothioisomunchnones to alkynes: Synthetic scope and mechanistic insights. Tetrahedron, 56, (9), 1247-1255. (doi:10.1016/S0040-4020(00)00022-3).

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Description/Abstract

This manuscript describes the regiospecific 1,3-dipolar cycloadditions of 2-aminothioisomunchnones (1-3) with methyl propiolate. The structure of compound 4 has been unequivocally determined by X-ray crystallography. Based on these experimental arguments and a theoretical rationale that supports the regiochemistry observed, a mechanistic pathway is discussed to account for the formation of pyridone or thiophene derivatives. The protocol has also been extended to the cycloadditions of aminothioisomunchnones derived from carbohydrates with dimethyl acetylenedicarboxylate to afford interesting glycosylaminoheterocycles.

Item Type: Article
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Keywords: dipolar cycloadditions, mesoionic compounds, pyridones, thiophenes, thioisomunchnonesmesoionic compounds, diastereoselective synthesis, acetylenicdipolarophiles, cycloaddition chemistry, systems
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19044
Date Deposited: 16 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/19044

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