Next Article in Journal
Natural Compounds from Saffron and Bear Bile Prevent Vision Loss and Retinal Degeneration
Next Article in Special Issue
Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride
Previous Article in Journal
Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids
Previous Article in Special Issue
A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(8), 13864-13874;

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
Received: 24 June 2015 / Revised: 22 July 2015 / Accepted: 24 July 2015 / Published: 30 July 2015
Full-Text   |   PDF [1082 KB, uploaded 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

Graphical abstract

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).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top