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Molecules 2015, 20(8), 13864-13874; doi:10.3390/molecules200813864

Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

School of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, Ireland
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Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 24 June 2015 / Revised: 22 July 2015 / Accepted: 24 July 2015 / Published: 30 July 2015
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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® 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, 1ʹ,2ʹ-dihydro-4ʹH-spiro[oxetane-3,3ʹ-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. View Full-Text
Keywords: annulation; cyclization; diazole; heterocycle; 4-membered rings annulation; cyclization; diazole; heterocycle; 4-membered rings
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Gurry, M.; McArdle, P.; Aldabbagh, F. Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole. Molecules 2015, 20, 13864-13874.

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