ABSTRACT
DEVELOPMENT OF NEW SYNTHETIC METHODOLOGIES FOR
ISOQUINOLONE AND ISOINDOLINONE DERIVATIVES
Mü / jde, Berk
M.Sc., Department of Chemistry
Supervisor: Prof. Dr. Metin Balci
July 2010, 146 pages
Due to the wide range of physiological activities, heterocycles containing nitrogen and
oxygen have always attracted the interest of chemists.
The objective of this research is to develop new synthetic routes to the synthesis of
isoquinolone and isoindolinone derivatives starting from 2-(2-carboxyethyl)benzoic acid
and homophthalic acid, respectively.
The half ester produced from 2-(2-carboxyethyl)benzoic acid was an important key
compound for the synthesis of new isoquinolone derivatives which are expected to be
biologically active. The corresponding acyl azides and isocyanates were generatedwhich might be used as a precursors to construct a variety of isoquinolone derivatives.
Transformation of acyl azides into urea derivatives followed by ring-closure under the
basic conditions provided isoquinolones.
Bromo- and methoxyhomophthalic acid derivatives were synthesized to increase in
variety of isoindolinone derivative. Then corresponding anhydrides were generated to
further reactions for synthesis of isoindolinone derivatives. Surprisingly, tetrazolinone
derivatives are also formed by 1,3 dipolar cycloaddition. Whole products were
conscientiously purified and characterized.
In addition, the similar methodology which was used for the synthesis of isoquinolone
derivatives, was applied to 2-(carboxymethyl)furan-3-carboxylic acid to synthesize new
nitrogen and oxygen containing heterocycles.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/3/12612145/index.pdf |
| Date | 01 July 2010 |
| Creators | Berk, Mujde |
| Contributors | Balci, Metin |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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