The Multicomponent Synthesis of Pyrroles from Cylcopropane S Using a One Pot Pd(0) Catalyzed Dehydrocarbonylation Protocol

Previous work done by the Kerr group has shown that tetrahydro-1,2-oxazines can be efficiently synthesized using a three component coupling reaction between a hydroxylamine, aldehyde and cyclopropane diester. This affords the desired heterocycle efficiently with a wide variety of substitution. When one esters bears an allyl group a Tsuji dehydrocarbonylation reaction may take place resulting in the formation of a 4,5-dihydro-1,2-oxazine. This motif contains a vinylogously acidic proton which is extremely labile and easily deprotonated. Under basic conditions this proton is removed and consequently the N-O bond is cleaved and subsequent condensation occurs forming a pyrrole. Using a sequence of chemical transformations specific pyrroles generated from the above methodology could be transformed into either BM 212 an anti-tuberculosis drug or Atorvastatin Calcium an anti-cholesterol drug. Each pharmaceutical will be derived using a three component coupling reaction and then conversion to a pyrrole followed by manipulations of the resulting functional groups.

Name thesis:degree_name

M Sc

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher

The University of Western Ontario

Year dc:date.issued

2012

Author dc:creator

• Humenny, William J

Advisor dc:contributor.advisor

• Michael Kerr

• Cyclopropanes
• nitrones
• tetrahydro-1
• 2-oxazines
• 4
• 5-dihydro-1
• pyrroles
• BM 212
• Atorvastatin Calcium
• dehydrocarbonylation

Language dc:language.iso

en_ca

Handle dc:identifier.uri

https://hdl.handle.net/20.500.14721/30030

OAI identifier oai:identifier

oai:uwo.scholaris.ca:20.500.14721/30030