I. [2 +2] Cycloaddition and benzannulation of 2-iodoynamides and application to the construction of highly substituted indoles : II. Synthesis of furo[2,3-g]thieno[2,3-e]indole via a benzannulation strategy

The synthesis and reactions of 2-iodoynamides were investigated. 2-Iodoynamides undergo efficient and regioselective [2 + 2] cycloaddition with ketene to produce cyclobutenones that are useful synthetic building blocks. Reaction of 2-iodoynamides and vinylketenes generated in situ from cyclobutenones proceeds via a pericyclic cascade mechanism to produce highly substituted 2-iodoanilines. Tandem strategies for the synthesis of highly substituted indoles involving this benzannulation reaction were investigated. In addition, the synthesis of furo[2,3-g]thieno[2,3- e]indole, a new tetracyclic aromatic compound, was achieved via a strategy based on benzannulation with ynamides.

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2015

Author dc:creator

• Wang, Yu-Pu, Ph. D. Massachusetts Institute of Technology

• Chemistry.

Statement dc:rights

• M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission.

Licence dc:rights.uri

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

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/101556

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/101556