Dissertations, Theses, and Capstone Projects
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.
Recommended Citation
Wu, Jing, "Heterocycle Synthesis from Quinols" (2019). CUNY Academic Works.
https://academicworks.cuny.edu/gc_etds/3269
Included in
Heterocyclic Compounds Commons, Organic Chemicals Commons, Pharmaceutical Preparations Commons