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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.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
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.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
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.

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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

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Date deposited: 18 Jul 2006
Last modified: 15 Jul 2019 19:01

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Contributors

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

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