Synthesis of pyridines and azaindoles via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes

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.

Name thesis:degree_name

Doctoral

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2019

Author dc:creator

• Bartko, Samuel G.(Samuel Garrett)

Advisor dc:contributor.advisor

• Rick Lane Danheiser.

• Chemistry.

Statement dc:rights

• 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.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/124044

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/124044