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-fuse...
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MDPI AG
2015-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/8/13864 |
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doaj-7b17d793154e402f809460b61d7c3f732020-11-24T21:37:05ZengMDPI AGMolecules1420-30492015-07-01208138641387410.3390/molecules200813864molecules200813864Synthesis of a Spirocyclic Oxetane-Fused BenzimidazoleMichael Gurry0Patrick McArdle1Fawaz Aldabbagh2School of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, IrelandSchool of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, IrelandSchool of Chemistry, National University of Ireland Galway, University Road, Galway SW4 NUI, IrelandA 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.http://www.mdpi.com/1420-3049/20/8/13864annulationcyclizationdiazoleheterocycle4-membered rings |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Michael Gurry Patrick McArdle Fawaz Aldabbagh |
| spellingShingle |
Michael Gurry Patrick McArdle Fawaz Aldabbagh Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole Molecules annulation cyclization diazole heterocycle 4-membered rings |
| author_facet |
Michael Gurry Patrick McArdle Fawaz Aldabbagh |
| author_sort |
Michael Gurry |
| title |
Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole |
| title_short |
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_sort |
synthesis of a spirocyclic oxetane-fused benzimidazole |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2015-07-01 |
| 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. |
| topic |
annulation cyclization diazole heterocycle 4-membered rings |
| url |
http://www.mdpi.com/1420-3049/20/8/13864 |
| work_keys_str_mv |
AT michaelgurry synthesisofaspirocyclicoxetanefusedbenzimidazole AT patrickmcardle synthesisofaspirocyclicoxetanefusedbenzimidazole AT fawazaldabbagh synthesisofaspirocyclicoxetanefusedbenzimidazole |
| _version_ |
1725938351695986688 |