Synthesis of pyridines and azaindoles via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes
Name
1141867125-MIT.pdf
Size
27.26 MB
Format
Adobe PDF
Checksum (MD5)
48c7ebb18d8ba8c05ca05b926773960f
Author(s)
Bartko, Samuel G.(Samuel Garrett)
Advisor(s)
Rick Lane Danheiser.
Alternative Title
Synthesis of pyridines via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes
Date Issued
2019
Publisher
Massachusetts Institute of Technology
Abstract
Pyridines are an important class of heterocycle with widespread applications in a variety of areas. The efficient synthesis of highly substituted pyridines is an ongoing goal of modem synthetic chemistry. Part I of this thesis describes a new synthetic strategy for the synthesis of highly substituted pyridines and azaindoles involving Diels-Alder reactions of vinyl- and heteroarylallenes with tosyl cyanide. The synthetic elaboration of the various pyridine products via an ipso substitution strategy is also described. Part II of this thesis describes the optimization and scale-up of a reproducible synthesis of 1-iodopropyne, an important building block chemical with widespread applications in a variety of transformations.
Description
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2019
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
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