Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

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-fu...

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Detalles Bibliográficos
Autores principales: Gurry, Michael, McArdle, Patrick, Aldabbagh, Fawaz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332447/
https://www.ncbi.nlm.nih.gov/pubmed/26263961
http://dx.doi.org/10.3390/molecules200813864
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author Gurry, Michael
McArdle, Patrick
Aldabbagh, Fawaz
author_facet Gurry, Michael
McArdle, Patrick
Aldabbagh, Fawaz
author_sort Gurry, Michael
collection PubMed
description 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.
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spelling pubmed-63324472019-01-24 Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole Gurry, Michael McArdle, Patrick Aldabbagh, Fawaz Molecules Article 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. MDPI 2015-07-30 /pmc/articles/PMC6332447/ /pubmed/26263961 http://dx.doi.org/10.3390/molecules200813864 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Gurry, Michael
McArdle, Patrick
Aldabbagh, Fawaz
Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title_full Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title_fullStr Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title_full_unstemmed Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title_short Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
title_sort synthesis of a spirocyclic oxetane-fused benzimidazole
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332447/
https://www.ncbi.nlm.nih.gov/pubmed/26263961
http://dx.doi.org/10.3390/molecules200813864
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AT mcardlepatrick synthesisofaspirocyclicoxetanefusedbenzimidazole
AT aldabbaghfawaz synthesisofaspirocyclicoxetanefusedbenzimidazole

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