New synthetic methods for biologically active aromatic heterocycles

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2010-01-01
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Gupta, Vinayak
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George A. Kraus
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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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The Department of Chemistry was founded in 1880.

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Abstract

First part of this work details the use of phosphazene base P4t–Bu mediated cyclodehydration towards the synthesis of heterocycles like 5,6–dihydroindolo[2,1–a]isoquinolines and 2,3–diarylbenzo[b]furans. This work also report the use of P4t–Bu for the total syntheses of O–methylcryptaustoline iodide and amurensin H. Both total syntheses feature P4t–Bu mediated cyclodehydration as the key steps towards the completion of the syntheses.

The second part of this work is dedicated towards the synthetic efforts to develop pyrido[2,3–d]pyrimidines as effective abelson kinase inhibitors. We successfully identified compounds with comparable or higher kinase inhibitory activity than Imatinib. We also successfully developed compounds which are more aqueous soluble than PD173955, an issue which has limited its use as a drug.

The third and final part of this work describes a novel and divergent methodology developed towards the syntheses of flavonoids like aurones, flavones and flavonols. This methodology describes the synthesis of a benzofuran derivative and a chromone intermediate which can be used to synthesis libraries of aurones and flavones in one step sequence respectively.

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Fri Jan 01 00:00:00 UTC 2010