Annelation of Aromatic Compounds via 1-Aminoisobenzofurans

The annelation of aromatic amides via 1-aminoisobenzofurans as transient reaction intermediates are reported. Three different methodologies are developed for generation of the aminoisobenzofurans in the presence of dienophiles. These involve: (1) the decomposition of an N,N-diisopropyl-o-((alpha)-diazomethyl) aromatic amide in the presence of a catalyst, (2) cesium fluoride induced (alpha)-elimination of an N,N-diisopropyl-o-((alpha),(alpha)'-bromotrimethylsilylmethyl)benzamide and (3) 2,2',6,6'-tetramethyl-piperidine induced 1,4-elimination of the cyclic imidate salt. In all cases, precursors can be synthesized by o-lithiation methodology.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Chen, Chin-Wen

• Chemistry, Organic

Identifier

(UMI)AAI8600145

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70307