Semester
Fall
Date of Graduation
2001
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Kung K. Wang.
Abstract
The development of a general route to the N-[2-(1-alkynyl)phenyl]ketenimines (enyne-ketenimines) and N-[2-(1-alkynyl)phenyl]carbodiimides (enyne-carbodiimides) and their subsequent thermal behavior are described. Like enyne-allene and enyne-ketene systems, these enyne-hetereocumulenes undergo cycloaromatization through two competing biradical mechanisms under thermal conditions and therefore could serve as potential DNA cleaving agents. The resultant nitrogen-containing hetereocyclic compounds are also biologically interesting. The research described herein provides a easy access to the synthesis of benzo[b]carbazole, indoloquinoline and indolonaphthyridine alkaloids. In addition, the new synthetic strategies for these compounds are very versatile, providing access to a diverse array of analogs of these alkaloids.
Recommended Citation
Shi, Chongsheng, "Synthesis of benzocarbazoles, indoloquinolines and indolonaphthridines from thermolysis of benzoenynyl ketenimines and carbodiimides" (2001). Graduate Theses, Dissertations, and Problem Reports. 1444.
https://researchrepository.wvu.edu/etd/1444
