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Synthesis of 2,3-disubstituted azaindoles using copper catalysts Shen, Yue

Abstract

The copper catalyzed reaction between 2-amino-3-halopyridines and 𝛽-dicarbonyl and related compounds was investigated. Twelve examples of azaindoles synthesis was observed in yields varying from 10-80%. The reaction of 𝛽-keto sulfones was complicated by the formation of 3-(phenylsulfonyl)pyridin-2-amine as a coproduct. Experiments to determine the timing of bond forming events were conducted, although synthetic challenges using amino substituted pyridines complicated these studies.

Item Metadata

Title
Synthesis of 2,3-disubstituted azaindoles using copper catalysts
Creator
Shen, Yue
Publisher
University of British Columbia
Date Issued
2019
Description
The copper catalyzed reaction between 2-amino-3-halopyridines and 𝛽-dicarbonyl and related compounds was investigated. Twelve examples of azaindoles synthesis was observed in yields varying from 10-80%. The reaction of 𝛽-keto sulfones was complicated by the formation of 3-(phenylsulfonyl)pyridin-2-amine as a coproduct. Experiments to determine the timing of bond forming events were conducted, although synthetic challenges using amino substituted pyridines complicated these studies.
Genre
Thesis/Dissertation
Type
Text
Language
eng
Date Available
2019-04-23
Provider
Vancouver : University of British Columbia Library
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International
DOI
10.14288/1.0378380
URI
http://hdl.handle.net/2429/69883
Degree
Master of Science - MSc
Program
Chemistry
Affiliation
Science, Faculty of; Chemistry, Department of
Degree Grantor
University of British Columbia
Graduation Date
2019-05
Campus
UBCV
Scholarly Level
Graduate
Rights URI
http://creativecommons.org/licenses/by-nc-nd/4.0/
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Attribution-NonCommercial-NoDerivatives 4.0 International