1-Aza-1'-Oxa(3,3)sigmatropic rearrangement: Synthesis of N-alkylindoles and 2,3-Dihydro-1h-Pyrrolo (1,2-A) Indole-9-Carboxylates

The {3,3}sigmatropic rearrangement of N-alkyl-N-aryl-O-acetoacetylhydroxylamines gives N-alkyl indoles in moderate yields under mild conditions. The substituted hydroxylamines were prepared by the condensation of aldehydes and ketones with an arylhydroxylamine and reduction of the nitrone so formed with sodium cyanoborohydride. This procedure affords high yields of N-alkyl-N-arylhydroxylamines and is tolerant of a wide variety of substituents.

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

• Hutchins, Charles William

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8026528

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67231