2026-09-20T22:58:42Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/1240442026-06-16T18:52:51Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Rick Lane Danheiser.
Bartko, Samuel G.(Samuel Garrett)
Massachusetts Institute of Technology. Department of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2020-03-09T18:50:47Z
2020-03-09T18:50:47Z
2019
2019
https://hdl.handle.net/1721.1/124044
1141867125
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2019
Cataloged from PDF version of thesis.
Includes bibliographical references.
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.
by Samuel G. Bartko.
Ph.D.
Ph.D. Massachusetts Institute of Technology, Department of Chemistry
254 pages
eng
Massachusetts Institute of Technology
MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission.
http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Synthesis of pyridines and azaindoles via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes
Synthesis of pyridines via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes
Thesis
application/pdf
2020-03-09T18:50:46Z
Publication
Doctoral
Chem
unknown
unknown
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<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.</Abstract>
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