Journal article
Intramolecular cyclization manifolds of 4-alkylpyridines bearing ambiphilic side chains: construction of spirodihydropyridines or benzylic cyclization via anhydrobase intermediates
Journal of organic chemistry, Vol.77(18), pp.8038-8048
09/21/2012
DOI: 10.1021/jo301247c
PMID: 22935010
Abstract
4-Alkylpyridines possessing nucleophilic β-dicarbonyl side chains have been converted to spirodihydropyridines upon treatment with ethyl chloroformate and sub-stoichiometric amounts of Ti(O(i)Pr)(4). Alternatively, inclusion of mild base in the reaction medium was found to facilitate generation of anhydrobase intermediates. Subsequent aldol-like condensations with electrophilic side chain moieties followed by hydrolysis delivered benzylically cyclized pyridines in good yield. In situ hydrogenation of cyclized anhydrobase intermediates afforded 4-substituted piperidines.
Details
- Title: Subtitle
- Intramolecular cyclization manifolds of 4-alkylpyridines bearing ambiphilic side chains: construction of spirodihydropyridines or benzylic cyclization via anhydrobase intermediates
- Creators
- Sharavathi G Parameswarappa - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USAF Christopher Pigge
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.77(18), pp.8038-8048
- DOI
- 10.1021/jo301247c
- PMID
- 22935010
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Language
- English
- Date published
- 09/21/2012
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9983985952302771
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