Date of Degree

5-2019

Document Type

Dissertation

Degree Name

Ph.D.

Program

Chemistry

Advisor

Shengping Zheng

Committee Members

Akira Kawamura

Mahesh Lakshman

David R. Mootoo

Subject Categories

Heterocyclic Compounds | Organic Chemicals | Pharmaceutical Preparations

Keywords

one-pot, cascade, acridone, carbazole, indolin-3-one, jaboticabin

Abstract

Three cascade reactions that provide access to various heterocyclic skeletons from quinols were developed. Various substituted 1-hydroxyacridones, 4-hydroxycarbazoles and 4-hydroxy-indolin-3-ones were readily synthesized in moderate to excellent yields. The common sequential transformation involves carbamation/Michael addition/mixed Claisen condensation/decarboxylative aromatization which were realized in one-pot reactions in the synthesis of acridones and indolin-3-ones, or two-step reactions in the synthesis of carbazoles. A side reaction from oxidative dearomatization of phenols, affording iodo diaryl ethers in one step from commercial phenols, albeit in low yields, revealed an intricate mechanistic pathway. The synthesis of jaboticabin was realized in nine linear steps from commercial phloroglucinol and 3,4-dihydroxybenzoic acid. In vivo experiments were undertaken and synthetic derivatives were made for future SAR studies.

This work is embargoed and will be available for download on Sunday, May 31, 2020

Graduate Center users:
To read this work, log in to your GC ILL account and place a thesis request.

Non-GC Users:
See the GC’s lending policies to learn more.

Share

COinS