Development of new synthetic methodologies for the synthesis of unusual isocoumarin and indole derivatives:The chemistry of homophthalic acid

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2007
Özcan, Sevil
Many heterocyclic compounds containing nitrogen, oxygen and sulfur show wide range of physiological activities and their synthesis has always been attracted the interest of chemists. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of isocoumarines, indoles, isoquinolines, benzodiazepinones and quinazolines, which have been found to show important biological activities. Starting from homophthalic acid and bishomophthalic acid the corresponding acyl azides were proposed to be synthesized, which then would be used for the synthesis of various heterocycles. The proposed diazide from homophthalic was not formed due to the tendency of the ortho-positioned acid to undergo cyclization. Instead, new unusual benzochromen and isocoumarin derivatives have been synthesized in a single step, for which reasonable mechanisms have been proposed. The half ester produced from homophthalic acid was an important key compound for the synthesis of new highly substituted indole derivatives, which are expected to be biologically active. The diisocyanate derived from was synthesized directly from ortho-bromo xylene was treated with alcohols and hydrazine to produce seven membered rings. Instead of the intramolecular cyclization reaction, they underwent polymerization to form new polymers. Furthermore, new synthetic method for the synthesis of pyrazoles has been developed.

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Citation Formats
S. Özcan, “Development of new synthetic methodologies for the synthesis of unusual isocoumarin and indole derivatives:The chemistry of homophthalic acid,” Ph.D. - Doctoral Program, Middle East Technical University, 2007.