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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Official URL: http://dx.doi.org/10.1016/S0040-4020(00)00022-3
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 |
|---|---|
| Uncontrolled Keywords: | dipolar cycloadditions, mesoionic compounds, pyridones, thiophenes, thioisomunchnonesmesoionic compounds, diastereoselective synthesis, acetylenicdipolarophiles, cycloaddition chemistry, systems |
| Related URLs: | http://dx.doi.org/10.1016/S004...00)00022-3 |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 19044 |
| URI: | http://eprints.soton.ac.uk/id/eprint/19044 |
| Deposited On: | 16 Dec 2005 |
| Last Modified: | 01 Jun 2011 02:46 |
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