3+2 -cycloadditions of 2-aminothioisomunchnones to alkynes: Synthetic scope and mechanistic insights
3+2 -cycloadditions of 2-aminothioisomunchnones to alkynes: Synthetic scope and mechanistic insights
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.
dipolar cycloadditions, mesoionic compounds, pyridones, thiophenes, thioisomunchnonesmesoionic compounds, diastereoselective synthesis, acetylenicdipolarophiles, cycloaddition chemistry, systems
1247-1255
Arevalo, M. J.
ac74db6e-6a83-4c60-b83e-e66995558d8f
Avalos, M.
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Babiano, R.
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Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Hursthouse, M. B.
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Jimenez, J. L.
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Light, M. E.
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Lopez, I.
2f91f6ce-61a3-4131-97ab-bb924030050d
Palacios, J. C.
51c8b47c-ec5d-49f7-ba86-f76039defccc
25 February 2000
Arevalo, M. J.
ac74db6e-6a83-4c60-b83e-e66995558d8f
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jimenez, J. L.
ea472a9b-29e7-46c1-8eb8-13616abf5492
Light, M. E.
5f2f6119-008d-4681-8ea0-e32559c94ddd
Lopez, I.
2f91f6ce-61a3-4131-97ab-bb924030050d
Palacios, J. C.
51c8b47c-ec5d-49f7-ba86-f76039defccc
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), .
(doi:10.1016/S0040-4020(00)00022-3).
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.
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More information
Published date: 25 February 2000
Keywords:
dipolar cycloadditions, mesoionic compounds, pyridones, thiophenes, thioisomunchnonesmesoionic compounds, diastereoselective synthesis, acetylenicdipolarophiles, cycloaddition chemistry, systems
Identifiers
Local EPrints ID: 19044
URI: http://eprints.soton.ac.uk/id/eprint/19044
ISSN: 0040-4020
PURE UUID: d1c8c527-d437-478e-a6cd-25107cfea56f
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Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:10
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Contributors
Author:
M. J. Arevalo
Author:
M. Avalos
Author:
R. Babiano
Author:
P. Cintas
Author:
J. L. Jimenez
Author:
M. E. Light
Author:
I. Lopez
Author:
J. C. Palacios
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