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Reactivity of 2-methyl thioisomunchnone with acid chlorides

Reactivity of 2-methyl thioisomunchnone with acid chlorides
Reactivity of 2-methyl thioisomunchnone with acid chlorides
This work describes the reactivity of 2-alkyl thioisomunchnones, exemplified here by the 2-methyl derivative, which behaves as nucleophile in the presence of both aliphatic and aromatic acid chlorides to give 2-heteroaryl ketones or 2-heteroaryl-1,3-diketones, respectively. However, 2-alkyl thioisomunchnones exhibit its characteristic 1,3-dipole behavior toward unsaturated systems.
cycloadditions, 1, 3-dicarbonyl compounds, mesoionics, tautomerism, thioisomunchnonesmesoionic compounds, derivatives, systems
0040-4039
4657-4660
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Diaz, J.
2efef4ad-69a7-453c-817f-ee83b63f8ed1
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jimenez, J. L.
ea472a9b-29e7-46c1-8eb8-13616abf5492
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Lopez, I.
2f91f6ce-61a3-4131-97ab-bb924030050d
Palacios, J. C.
51c8b47c-ec5d-49f7-ba86-f76039defccc
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Diaz, J.
2efef4ad-69a7-453c-817f-ee83b63f8ed1
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jimenez, J. L.
ea472a9b-29e7-46c1-8eb8-13616abf5492
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Lopez, I.
2f91f6ce-61a3-4131-97ab-bb924030050d
Palacios, J. C.
51c8b47c-ec5d-49f7-ba86-f76039defccc

Avalos, M., Babiano, R., Cintas, P., Diaz, J., Hursthouse, M. B., Jimenez, J. L., Light, M. E., Lopez, I. and Palacios, J. C. (2003) Reactivity of 2-methyl thioisomunchnone with acid chlorides. Tetrahedron Letters, 44 (25), 4657-4660. (doi:10.1016/S0040-4039(03)01087-6).

Record type: Article

Abstract

This work describes the reactivity of 2-alkyl thioisomunchnones, exemplified here by the 2-methyl derivative, which behaves as nucleophile in the presence of both aliphatic and aromatic acid chlorides to give 2-heteroaryl ketones or 2-heteroaryl-1,3-diketones, respectively. However, 2-alkyl thioisomunchnones exhibit its characteristic 1,3-dipole behavior toward unsaturated systems.

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More information

Published date: 16 June 2003
Keywords: cycloadditions, 1, 3-dicarbonyl compounds, mesoionics, tautomerism, thioisomunchnonesmesoionic compounds, derivatives, systems

Identifiers

Local EPrints ID: 19883
URI: http://eprints.soton.ac.uk/id/eprint/19883
ISSN: 0040-4039
PURE UUID: 5759255e-de76-4219-b8ee-2ae5e0afbc05
ORCID for M. E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 09 Jan 2022 02:59

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Contributors

Author: M. Avalos
Author: R. Babiano
Author: P. Cintas
Author: J. Diaz
Author: J. L. Jimenez
Author: M. E. Light ORCID iD
Author: I. Lopez
Author: J. C. Palacios

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