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New Methods for Heterocycle Preparation

Maciejewski, John Paul (2011) New Methods for Heterocycle Preparation. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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This dissertation will describe the development and application of novel methods for heterocycle preparation. The first chapter will outline the development of a titanocene catalyzed epoxide-opening rearrangement to prepare indolines from epoxyanilines. A discussion of the reaction development, along with the substrate scope and limitations will be reported.The second chapter will describe progress toward expanding the scope of aStaudinger/aza-Wittig reaction used to prepare substituted 1,2,4-triazines. This methodology has been applied towards the synthesis of a model system for the DEF rings of the natural product noelaquinone. The challenges associated with the Staudinger/aza-Wittig reaction, and the late-stage oxidation strategy to prepare the DEF rings of the noelaquinone model system will be discussed.The third chapter will describe the importance and general preparation of (E)-alkene peptide isosteres. Using compounds prepared in the UPCMLD and published on PubChem as a reference, we present our ongoing initiative to expand the library of α,β-cyclopropyl-γ-amino acid analogs.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Maciejewski, John Pauljpm53@pitt.eduJPM53
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peter
Committee MemberDay, Billy
Committee MemberCurran, Dennis
Committee MemberFloreancig, Paul
Date: 30 June 2011
Date Type: Completion
Defense Date: 3 March 2011
Approval Date: 30 June 2011
Submission Date: 30 March 2011
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: azide; radical cyclization; azaindoline; peptide mimic
Other ID:, etd-03302011-150740
Date Deposited: 10 Nov 2011 19:33
Last Modified: 15 Nov 2016 13:37


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