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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), pp. 1247-1255. (doi:10.1016/S0040-4020(00)00022-3).

Record type: Article


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.

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Published date: 25 February 2000
Keywords: dipolar cycloadditions, mesoionic compounds, pyridones, thiophenes, thioisomunchnonesmesoionic compounds, diastereoselective synthesis, acetylenicdipolarophiles, cycloaddition chemistry, systems


Local EPrints ID: 19044
ISSN: 0040-4020
PURE UUID: d1c8c527-d437-478e-a6cd-25107cfea56f

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Date deposited: 16 Dec 2005
Last modified: 17 Jul 2017 16:34

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Author: M. J. Arevalo
Author: M. Avalos
Author: R. Babiano
Author: P. Cintas
Author: M. B. Hursthouse
Author: J. L. Jimenez
Author: M. E. Light
Author: I. Lopez
Author: J. C. Palacios

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