Journal article
Intramolecular cyclization of alkylimidazoles
Tetrahedron letters, Vol.56(23), pp.3204-3207
06/03/2015
DOI: 10.1016/j.tetlet.2014.12.074
Abstract
[Display omitted] 1,2-Dialkylimidazoles can be converted to nucleophilic 2-alkylidene imidazolines upon treatment with (BOC)2O under mild conditions. Incorporation of a β-keto amide carbonyl electrophile in the 2-alkylimidazole side chain results in intramolecular aldol-like cyclization to afford imidazole-functionalized γ-lactams. Positioning of a ketone electrophile in a 1-alkyl side chain results in cyclization at the 2-position to afford fused ring imidazoles through a similar reaction manifold. Efficient transfer of a BOC group from an intermediate N-acyl imidazolium species to a nucleophilic center in the cyclized product appears to be an important feature of these reactions.
Details
- Title: Subtitle
- Intramolecular cyclization of alkylimidazoles
- Creators
- Madhur S JoshiAshabha I LansakaraF. Christopher Pigge
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.56(23), pp.3204-3207
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/j.tetlet.2014.12.074
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Grant note
- DOI: 10.13039/100000001, name: U.S. National Science Foundation, award: CHE-1265488
- Language
- English
- Date published
- 06/03/2015
- Academic Unit
- Chemistry; Radiology
- Record Identifier
- 9983985875902771
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