Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Tandem Allylic Isomerization – IMDAF Reactions and Other Isomerizations

Xu, Jie (2013) Tandem Allylic Isomerization – IMDAF Reactions and Other Isomerizations. Master's Thesis, University of Pittsburgh. (Unpublished)

Primary Text

Download (19MB) | Preview


The first section of this thesis describes a novel allylic isomerization, followed by an intra-molecular Diels-Alder furan cycloaddition, fragmentation, aromatization, and N-Boc deprotection cascade that leads to the formation of synthetically and biologically useful 5,6,7-substituted indoles. Various 5,6,7-substituted indoles are synthesized in moderate to good yield using this convergent method. Nonthermal microwave effects also prove to be essential in this transformation.
The second section describes the extension of our indole synthesis methodology through a microwave assisted intramolecular Diels-Alder furan cycloaddition to a 5-hydroxyindole synthesis from readily available alkynals and alkynones. This convergent procedure is compatible with multiple-functionalities in the 4-position of the indole, including electron-withdrawing and electron-donating groups. Yields range from 44 to 64%.
The third section describes a methodology study of the alkyne isomerization reaction using a non-nucleophilic base. After screening of reaction conditions, optimal conditions were achieved by the use of 2.2 equiv of LiTMP in THF (1.0 M substrate concentration) at r.t. for 1 h.


Social Networking:
Share |


Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Xu, Jiejix31@pitt.eduJIX31
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Date: 18 October 2013
Date Type: Publication
Defense Date: 10 April 2013
Approval Date: 18 October 2013
Submission Date: 12 April 2013
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 230
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Isomerization; Indole; Intra-molecular Diels-Alder Furan Reaction; Palladium; Cascade; Microwave
Date Deposited: 18 Oct 2013 14:44
Last Modified: 15 Nov 2016 14:11


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item