Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

Molecules

Michael Gurry²  Patrick McArdle²  Fawaz Aldabbagh¹ 

[1] School of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, Ireland;

关键词: annulation;    cyclization;    diazole;    heterocycle;    4-membered rings;   

DOI  :  10.3390/molecules200813864

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.