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
Open AccessArticle

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; https://doi.org/10.3390/molecules200813864
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
Show Figures

Graphical abstract

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

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop