Development of new methodologies for the synthesis of thienopyridazinone and furo- and thienodiazepinedione derivatives

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2013
Özer, Merve Sinem
Some heterocycles are natural compounds and play a major part in biochemical processes. They also have interesting biological activities and pharmacological properties. In this study, new methodologies were developed to synthesize bicyclic heterocyclic compounds consisting of thiophene and furan fused to six- and seven-membered rings, respectively. In the first part, thienopyridazinone derivatives were synthesized. For this purpose, the starting compound was chosen as methyl 2-(2-methoxy-2-oxoethyl)-3-thienoate, which was oxidized with SeO2 and then treated with hydrazine derivatives for cyclization. Later, they were converted to isocyanate derivatives which were used to produce the corresponding urethane and/or amine derivatives by treatment with methanol and aqueous HCl, respectively. In the second part, a new synthetic methodology was developed for furo- or thienodiazepinedione derivatives starting from methyl 2-(2-methoxy-2-oxoethyl)-3-furoate or-thionate. First, acyl azides were synthesized. Application of Curtius rearrangement to acyl azides gave the corresponding isocyantes, which was followed by cyclzation rection to produce the desired compound.
Citation Formats
M. S. Özer, “Development of new methodologies for the synthesis of thienopyridazinone and furo- and thienodiazepinedione derivatives,” M.S. - Master of Science, Middle East Technical University, 2013.