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Synthesis of a spirocyclic oxetane-fused benzimidazole

Gurry, Michael
; 
McArdle, Patrick
; 
Aldabbagh, Fawaz
Identifiers
http://hdl.handle.net/10379/11777
https://doi.org/10.13025/28734
Repository DOI
10.3390/molecules200813864
Publication Date
2015-07-30
Keywords
annulation, cyclization, diazole, heterocycle, 4-membered rings, drug discovery
Type
Article
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Citation
Gurry, Michael; McArdle, Patrick; Aldabbagh, Fawaz (2015). Synthesis of a spirocyclic oxetane-fused benzimidazole. Molecules 20 (8), 13864-13874
Abstract
A new synthesis of 2-oxa-7-azaspiro[3.5]nonane is described. Spirocyclic oxetanes, including 2-oxa-6-azaspiro[3.3]heptane were converted into o-cycloalkylaminoacetanilides for oxidative cyclizations using Oxone((R)) in formic acid. The expanded spirocyclic oxetane successfully gave the [1,2-a] ring-fused benzimidazole. X-ray crystal structure of the resultant new tetracyclic system, 1',2'-dihydro-4'H-spiro[oxetane-3,3'-pyrido[1,2-a]benzimidazole] and the azetidine ring-opened adduct, N-(2-acetamido-4-bromophenyl)-N-{[3-(chloromethyl)oxetan-3-yl]methyl}acetamide are disclosed.
Funder
Publisher
MDPI AG
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
cbn
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Externally hosted open access publications with University of Galway authors (2)