The University of Southampton
University of Southampton Institutional Repository

Expeditious formation of 1,2,4-triazine derivatives via a thioisomünchnone cycloaddition reaction

Expeditious formation of 1,2,4-triazine derivatives via a thioisomünchnone cycloaddition reaction
Expeditious formation of 1,2,4-triazine derivatives via a thioisomünchnone cycloaddition reaction
A novel type of heterocyclization reaction involving the [3+2] cycloaddition of N,N-dialkylamino-substituted thioisomunchnones with azodicarboxylates gives rise to 1,2,4-triazine derivatives after a selective fragmentation pathway of the transient cycloadducts. The X-ray analysis of 7 accounts for the fate of this particular transformation. An asymmetric version using chiral carbohydrate-based thioisomunchnones has also been disclosed.
diastereoselective synthesis, mesoionic compounds, mesomeric betaines, systems, dipolarophiles, chemistry, dipoles
0040-4039
8675-8678
Arévalo, Maria J.
7f940557-6cf5-4e72-9478-2bc5154fb06b
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Arévalo, Maria J.
7f940557-6cf5-4e72-9478-2bc5154fb06b
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f

Arévalo, Maria J., Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Hursthouse, Michael B., Jiménez, José L., Light, Mark E., López, Ignacio and Palacios, Juan C. (1999) Expeditious formation of 1,2,4-triazine derivatives via a thioisomünchnone cycloaddition reaction. Tetrahedron Letters, 40 (49), 8675-8678. (doi:10.1016/S0040-4039(99)01837-7).

Record type: Article

Abstract

A novel type of heterocyclization reaction involving the [3+2] cycloaddition of N,N-dialkylamino-substituted thioisomunchnones with azodicarboxylates gives rise to 1,2,4-triazine derivatives after a selective fragmentation pathway of the transient cycloadducts. The X-ray analysis of 7 accounts for the fate of this particular transformation. An asymmetric version using chiral carbohydrate-based thioisomunchnones has also been disclosed.

This record has no associated files available for download.

More information

Published date: 1999
Keywords: diastereoselective synthesis, mesoionic compounds, mesomeric betaines, systems, dipolarophiles, chemistry, dipoles

Identifiers

Local EPrints ID: 39136
URI: http://eprints.soton.ac.uk/id/eprint/39136
ISSN: 0040-4039
PURE UUID: 610920e5-fa73-4736-90ad-9c609cddf811

Catalogue record

Date deposited: 18 Jul 2006
Last modified: 15 Mar 2024 08:11

Export record

Altmetrics

Contributors

Author: Maria J. Arévalo
Author: Martin Avalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: José L. Jiménez
Author: Mark E. Light
Author: Ignacio López
Author: Juan C. Palacios

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 http://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.

×