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The synthesis of 1,2,7,11b-tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5h)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5h)-ones

Bourke, Sharon
; 
Heaney, Frances
Identifiers
http://hdl.handle.net/10379/8889
 https://doi.org/10.13025/24470
Publication Date
1995-10-01
Keywords
x=y-zh systems, 1,3-dipolar cycloaddition reactions, potential 1,3-dipoles, 1,3-azaprotio cyclotransfer, heterocyclic synthesis, organic azides, generation, nitrones, oximes, isoxazolo<4,3-c>quinolones
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journal article
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Bourke, Sharon; Heaney, Frances (1995). The synthesis of 1,2,7,11b-tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5h)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5h)-ones. Tetrahedron Letters 36 (41), 7527-7530
Abstract
The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H) (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.
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Publisher
Elsevier BV
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Externally hosted open access publications with University of Galway authors (1)