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Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

School of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, Ireland
Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Molecules 2015, 20(8), 13864-13874;
Received: 24 June 2015 / Revised: 22 July 2015 / Accepted: 24 July 2015 / Published: 30 July 2015
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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MDPI and ACS Style

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

AMA Style

Gurry M, McArdle P, Aldabbagh F. Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole. Molecules. 2015; 20(8):13864-13874.

Chicago/Turabian Style

Gurry, Michael, Patrick McArdle, and Fawaz Aldabbagh. 2015. "Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole" Molecules 20, no. 8: 13864-13874.

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