Author
McComb, Todd
Other Contributors
Archer, Sydney;
Date Issued
1989-05
Subject
Chemistry
Degree
MS;
Terms of Use
This electronic version is a licensed copy owned by Rensselaer Polytechnic Institute, Troy, NY. Copyright of original work retained by author.;
Abstract
The synthesis of 11 was examined towards the goal of preparing sufficient quantities for biological testing. The preliminary results of its activity against some human cancer tumor cells are presented.; The acid 1 was treated with thionyl chloride and then dimethyl amine to give the amide 2 in excellent yield. The reduction of this amide with lithium aluminum hydride followed by treatment with methyl iodide gave a good yield of the methiodide 1. The displacement of trimethylamine from 1 by heating it with potassium cyanide gave the nitrile 4 in low yield. Methanolysis of 4 cleanly gave the ester 5. The acid catalyzed condensation of 5 with 3-acetylpyridine followed by quaternization at the pyridine nitrogen with 4-nitrobenzyl bromide gave the salt 7 in good yield. The intermolecular ring closure that converted 7 into 8 occurred in nearly quantitative yield. The dequaternization of 8 by heating with tributylphosphine gave the ester 9 in an acceptable yield. Reduction of 9 with lithium aluminum hydride gave an excellent yield of the alcohol 10. Treatment of 10 with 4-dimethylaminopyridine and excess methyl isocyanate gave the title compound in an acceptable yield.;
Description
May 1989; School of Science
Department
Dept. of Chemistry;
Publisher
Rensselaer Polytechnic Institute, Troy, NY
Relationships
Rensselaer Theses and Dissertations Online Collection;
Access
Restricted to current Rensselaer faculty, staff and students. Access inquiries may be directed to the Rensselaer Libraries.;