The University of Southampton
University of Southampton Institutional Repository

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
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
0040-4020
1247-1255
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.
276e7125-0773-43f6-97e3-77106e9b6e8f
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.
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.
276e7125-0773-43f6-97e3-77106e9b6e8f
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), 1247-1255.

Record type: Article

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.

Full text not available from this repository.

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: https://eprints.soton.ac.uk/id/eprint/19044
ISSN: 0040-4020
PURE UUID: d1c8c527-d437-478e-a6cd-25107cfea56f

Catalogue record

Date deposited: 16 Dec 2005
Last modified: 04 Nov 2017 11:04

Export record

Contributors

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

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×