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Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening

Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening
Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening
Dihydroimidazole N-oxides 1 undergo 1,3-dipolar cycloaddition with alkyne dipolarophiles and the cycloadducts suffer isoxazoline N-O bond cleavage to afford ene-1,1-diamines, with subsequent cyclisation to pyrrolo[1,2-a]imidazole-5,6-diones if possible.
1359-7345
1949-1950
Jones, Raymond C.F.
a44c98ab-2e7e-4e02-860f-a9348d60ad08
Martin, Jason N.
74b907d7-6baf-4c44-962d-e0ae02ab10e4
Smith, Paul
5971135c-98d0-47e0-9f40-94085befbd20
Gelbrich, Tomas
47b0fb56-c71c-4fa3-a7b1-c7082eba78b0
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Jones, Raymond C.F.
a44c98ab-2e7e-4e02-860f-a9348d60ad08
Martin, Jason N.
74b907d7-6baf-4c44-962d-e0ae02ab10e4
Smith, Paul
5971135c-98d0-47e0-9f40-94085befbd20
Gelbrich, Tomas
47b0fb56-c71c-4fa3-a7b1-c7082eba78b0
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28

Jones, Raymond C.F., Martin, Jason N., Smith, Paul, Gelbrich, Tomas, Light, Mark E. and Hursthouse, Michael B. (2000) Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening. Chemical Communications, (19), 1949-1950. (doi:10.1039/b005530l).

Record type: Article

Abstract

Dihydroimidazole N-oxides 1 undergo 1,3-dipolar cycloaddition with alkyne dipolarophiles and the cycloadducts suffer isoxazoline N-O bond cleavage to afford ene-1,1-diamines, with subsequent cyclisation to pyrrolo[1,2-a]imidazole-5,6-diones if possible.

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Published date: 2000
Organisations: Chemistry

Identifiers

Local EPrints ID: 39125
URI: http://eprints.soton.ac.uk/id/eprint/39125
ISSN: 1359-7345
PURE UUID: 9fcfe406-ce91-47b1-8290-b2a9b0f580df

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Date deposited: 17 Jul 2006
Last modified: 15 Jul 2019 19:01

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