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MULTICOMPONENT REACTIONS FOR THE SYNTHESIS OF FLUORINATED ORGANIC COMPOUNDS AND RELATED CHEMISTRY
by
Inessa Bychinskaya
A Dissertation Presented to the
FACULTY OF THE USC GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
December 2011
Copyright 2011 Inessa Bychinskaya
Object Description
| Title | Multicomponent reactions for the synthesis of fluorinated organic compounds and related chemistry |
| Author | Bychinskaya, Inessa |
| Author email | bychinsk@usc.edu;inessa.bychinskaya@gmail.com |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts And Sciences |
| Date defended/completed | 2011-07-06 |
| Date submitted | 2011-10-31 |
| Date approved | 2011-11-01 |
| Restricted until | 2011-11-01 |
| Date published | 2011-11-01 |
| Advisor (committee chair) | Prakash, Surya |
| Advisor (committee member) |
Olah, George Petasis, Nicos Shing, Katherine |
| Abstract | Development of eco- and aqueous friendly, stable and recyclable catalysts for organic synthesis is one of the major steps in safe, environmentally benign and sustainable practice of chemistry. This dissertation is devoted to the preparation of novel solid Lewis acid catalysts and their application in the synthesis of both fluorinated and non-fluorinated biologically important molecules. It focuses on the development of sustainable methodology for the synthesis of α-amino nitriles and variety of heterocyles such as 3,4- dihydropyrimidininones, benzimidazolines, dihydrobenzoxazinones, which serve as important building blocks for drug discovery. It also describes the new methodology for the synthesis of α-alkyl-α-fluoromethylenebisphosphonates. ❧ Chapter 1 gives a general review of solid acid catalysts and discusses their need in the development of ""green"" catalysis. ❧ Chapter 2 describes the synthesis of various α-amino nitriles, precursors of vital α-amino acids via Strecker reaction employing ""green"" catalysts such as Nafion-H and its silica nanocomposite Nafion SAC-13. Preparation of Nafion-Fe, a Lewis acid version of Nafion-H and its application in ketonic Strecker reaction are also described. ❧ In Chapter 3, an efficient one-pot synthesis of biologically important 3,4- dihydro-pyrimidininones by three-component Biginelli reaction employing Ga(OTf)₃ as catalyst is disclosed. The preparation of novel thiazine-type products and mechanism of their formation is discussed. ❧ In Chapter 4, the preparation and application of novel Lewis acid catalyst Nafion-Ga, gallium salt of Nafion-H in synthesis of 3,4- dihydropyrimidininones by Biginelli reaction and benzimidazolines, dihydrobenzoxazinones by condensation-cyclization reactions is expounded. ❧ Chapter 5 deals with the development of a new method for the synthesis of α-alkyl-α-fluoromethylenebisphosphonates, potential antiresorptive drugs. |
| Keyword | bening catalysis; biologically active compounds; multicomponent reactions; organofluorine compounds |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Provenance | Electronically uploaded by the author |
| Type | texts |
| Legacy record ID | usctheses-m |
| Rights | Bychinskaya, Inessa |
| Access conditions | The author retains rights to his/her dissertation, thesis or other graduate work according to U.S. copyright law. Electronic access is being provided by the USC Libraries in agreement with the author, as the original true and official version of the work, but does not grant the reader permission to use the work if the desired use is covered by copyright. It is the author, as rights holder, who must provide use permission if such use is covered by copyright. The original signature page accompanying the original submission of the work to the USC Libraries is retained by the USC Libraries and a copy of it may be obtained by authorized requesters contacting the repository e-mail address given. |
| Repository name | University of Southern California Digital Library |
| Repository address | USC Digital Library, University of Southern California, University Park Campus MC 7002, 106 University Village, Los Angeles, California 90089-7002, USA |
| Repository email | cisadmin@usc.edu |
| Archival file | uscthesesreloadpub_Volume71/etd-Bychinskay-381.pdf |
Description
| Title | Page 1 |
| Full text | MULTICOMPONENT REACTIONS FOR THE SYNTHESIS OF FLUORINATED ORGANIC COMPOUNDS AND RELATED CHEMISTRY by Inessa Bychinskaya A Dissertation Presented to the FACULTY OF THE USC GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) December 2011 Copyright 2011 Inessa Bychinskaya |
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