Development of a microwave-assisted epoxide aminolysis and investigation of the aza-cope rearrangement--mannich cyclization for alkaloid synthesis

<p>β-Amino alcohols are important organic compounds with numerous applications. Commonly β-amino alcohols are prepared by ring opening of epoxides using an amine nucleophile and a catalyst or promoter. Ring opening can take place by the SN1 pathway or the SN2 pathway, but no single catalyst or promoter consistently gives SN2 selectivity. Additionally, long reaction times are often required to obtain adequate yields. We have demonstrated that microwave heating reduces reaction times for the aminolysis of both reactive and unreactive, sterically hindered epoxides. These reactions were accomplished with various amines. In all cases, only one equivalent of amine and epoxide were needed to give good yields and modest to excellent regioselectivity for the SN2 product.</p> <p>Amino alcohols made by aminolysis and other methods were used to investigate the aza-Cope rearrangement—Mannich cyclization. We proposed that this procedure could be used to produce compounds we could modify and transform into several alkaloids.</p>

Name thesis:degree_name

Master of Science (MS)

Level thesis:degree_level

Open Access Thesis

Discipline thesis:degree_discipline

Chemistry

Year

2007

Author dc:creator

• D'Souza, Brendan Roberto

• Pharmaceutical chemistry technique
• Organic compounds synthesis
• Alkaloids
• Chemistry

Repository record dc:identifier

https://commons.emich.edu/theses/16

OAI identifier oai:identifier

oai:commons.emich.edu:theses-1015