| Iron(III) Chloride/Diorganyl Diselenides: A Tool for Intramolecular Cyclization of Alkynone O-Methyloximes. | |
| | |
MedLine Citation:
|
PMID: 23351114 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
This report describes the synthesis of 4-organoselenyl-isoxazoles via FeCl3/RSeSeR-mediated intramolecular cyclization of alkynone O-methyloximes. The optimized conditions allowed the cyclization to proceed at room temperature, under ambient atmosphere and the reaction requires a short time to be completed. The reaction conditions tolerated neutral, electron-donating and electron-withdrawing groups present in both substrates, alkynone O-methyloximes and diorganyl diselenides. Treatment of 4-organoselenyl-isoxazoles with n-butyl lithium, followed by trapping with electrophiles, furnished the functionalized isoxazoles in good yields. The obtained products also proved to be suitable substrates for the preparation of 4-bromo-isoxazoles via Br/Se exchange reaction. |
| | |
Authors:
|
Adriane Sperança; Benhur Godoi; Gilson Zeni |
Related Documents
:
|
16709454 - Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally ... 7853344 - N-acyl-2-substituted-1,3-thiazolidines, a new class of non-narcotic antitussive agents:... 23589324 - Catalytic asymmetric synthesis of spirooxindoles via addition of isothiocyanato oxindol... 15223074 - Complementation of sod-deficient escherichia coli by manganese porphyrin mimics of supe... 23288204 - Synthesis of n,n'-diglycosylated isoindigos. 18763774 - Origin of the regio- and stereoselectivity of allylic substitution of organocopper reag... |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2013-1-27 |
Journal Detail:
|
Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2013 Jan |
Date Detail:
|
Created Date: 2013-1-28 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Synthesis and Properties of Highly Dispersed Ionic Silica-Polyethylene Glycol Nanohybrids.
Next Document: Detailed analysis of biased histamine H(4) receptor signalling by JNJ 7777120 analogues.