Journal article
An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems
Journal of organic chemistry, Vol.67(13), pp.4547-4552
06/01/2002
DOI: 10.1021/jo0256181
PMID: 12076155
Abstract
A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.
Details
- Title: Subtitle
- An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems
- Creators
- F. Christopher Pigge - Department of Chemistry and Biochemistry, University of MissouriSt. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499Fatemeh Ghasedi - Department of Chemistry and Biochemistry, University of MissouriSt. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499Nigam P Rath - Department of Chemistry and Biochemistry, University of MissouriSt. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121-4499
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.67(13), pp.4547-4552
- DOI
- 10.1021/jo0256181
- PMID
- 12076155
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 06/01/2002
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216712802771
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