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Pyrrolo [1,2,3-de] quinoxalines: unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides

Pyrrolo [1,2,3-de] quinoxalines: unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides
Pyrrolo [1,2,3-de] quinoxalines: unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides
4,5-Dihydroimidazoles undergo an N-alkylation and 1,3-dipolar cycloaddition cascade with unsaturated ?-bromoketones, with subsequent eliminative ring-opening, recyclisation and tautomerisation to form unexpected hexahydropyrrolo[1,2,3-de]quinoxalines.
glycine binding-site, potent antagonists, pyrrolidines, pyrroloimidazoles, receptor
0040-4039
3951-3954
Jones, Raymond C. F.
50e973f9-3926-4126-bd59-4e2c0e9e8f98
Iley, James N.
b30fd482-e98a-440a-a13a-411d1c3bcdd3
Lory, Pedro M. J.
2212195a-ccc5-42c6-a276-8f65111a08f6
Coles, Simon C.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jones, Raymond C. F.
50e973f9-3926-4126-bd59-4e2c0e9e8f98
Iley, James N.
b30fd482-e98a-440a-a13a-411d1c3bcdd3
Lory, Pedro M. J.
2212195a-ccc5-42c6-a276-8f65111a08f6
Coles, Simon C.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Jones, Raymond C. F., Iley, James N., Lory, Pedro M. J., Coles, Simon C., Light, Mark E. and Hursthouse, Michael B. (2001) Pyrrolo [1,2,3-de] quinoxalines: unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides. Tetrahedron Letters, 42 (23), 3951-3954. (doi:10.1016/S0040-4039(01)00617-7).

Record type: Article

Abstract

4,5-Dihydroimidazoles undergo an N-alkylation and 1,3-dipolar cycloaddition cascade with unsaturated ?-bromoketones, with subsequent eliminative ring-opening, recyclisation and tautomerisation to form unexpected hexahydropyrrolo[1,2,3-de]quinoxalines.

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More information

Published date: 2001
Keywords: glycine binding-site, potent antagonists, pyrrolidines, pyrroloimidazoles, receptor
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Identifiers

Local EPrints ID: 39121
URI: http://eprints.soton.ac.uk/id/eprint/39121
DOI: doi:10.1016/S0040-4039(01)00617-7
ISSN: 0040-4039
PURE UUID: 947c2e64-51b5-4718-8014-608fe7809a27
ORCID for Simon C. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 21 Jun 2006
Last modified: 16 Mar 2024 03:05

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Contributors

Author: Raymond C. F. Jones
Author: James N. Iley
Author: Pedro M. J. Lory
Author: Simon C. Coles ORCID iD
Author: Mark E. Light ORCID iD
Author: Michael B. Hursthouse

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