Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

Michael Gurry; Patrick McArdle; Fawaz Aldabbagh

doi:10.3390/molecules200813864

Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

Michael Gurry, Patrick McArdle, Fawaz Aldabbagh

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

5 Citations (Scopus)

Abstract

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, 1',2'-dihydro-4'H-spiro[oxetane-3,3'-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.

Original language	English
Pages (from-to)	13864-13874
Number of pages	11
Journal	Molecules
Volume	20
Issue number	8
DOIs	https://doi.org/10.3390/molecules200813864
Publication status	Published - 1 Aug 2015
Externally published	Yes

Keywords

4-membered rings
Annulation
Cyclization
Diazole
Heterocycle

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10.3390/molecules200813864

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title = "Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole",

abstract = "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{\textregistered} 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, 1',2'-dihydro-4'H-spiro[oxetane-3,3'-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.",

keywords = "4-membered rings, Annulation, Cyclization, Diazole, Heterocycle",

author = "Michael Gurry and Patrick McArdle and Fawaz Aldabbagh",

note = "Publisher Copyright: {\textcopyright}2015 by the authors.",

year = "2015",

month = aug,

day = "1",

doi = "10.3390/molecules200813864",

language = "English",

volume = "20",

pages = "13864--13874",

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TY - JOUR

T1 - Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

AU - Gurry, Michael

AU - McArdle, Patrick

AU - Aldabbagh, Fawaz

PY - 2015/8/1

Y1 - 2015/8/1

N2 - 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, 1',2'-dihydro-4'H-spiro[oxetane-3,3'-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.

AB - 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, 1',2'-dihydro-4'H-spiro[oxetane-3,3'-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.

KW - 4-membered rings

KW - Annulation

KW - Cyclization

KW - Diazole

KW - Heterocycle

UR - http://www.scopus.com/inward/record.url?scp=84941248201&partnerID=8YFLogxK

U2 - 10.3390/molecules200813864

DO - 10.3390/molecules200813864

M3 - Article

SN - 1420-3049

VL - 20

SP - 13864

EP - 13874

JO - Molecules

JF - Molecules

IS - 8

ER -

Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole

Abstract

Keywords

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