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Nucleophilic addition to electron deficient indoles and the synthesis of fused heterocyclic ring systems.

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Call No.	Ph.D. 2010
Author	Alford, Philip E.
Title	Nucleophilic addition to electron deficient indoles and the synthesis of fused heterocyclic ring systems.
Date	2010
Abstract	The chemistry of indole can be reversed and redirected by the addition of powerful electron-withdrawing groups. Incorporation of a nitro group at C-2 or C-3 renders the adjacent carbon susceptible to nucleophilic attack. Nitro, cyano, and phenylsulfonyl indoles are each examined as potential Michael acceptors. Nucleophilic attack at C-3 has been demonstrated on 1,2-bis(phenylsulfonyl)indoles using organocuprates. Nucleophilic addition of hetaryllithium compounds to 3-nitro-1-(phenylsulfonyl)indole is described as a general method for the C-2 arylation of indoles. In addition to providing convenient access to 3-nitro-2-hetarylindoles, this investigation provides some insight into the nature and scope of the reaction. Electron-rich 3-aminoindoles are highly unstable intermediates that can be generated by reduction of the corresponding nitroindoles. Though the resulting 3-aminoindoles cannot be isolated, in situ acylation produces the amide. From these substrates, new tetracyclic _-carbolines containing the previously unknown 10Hindolo[3,2-b]thieno[2,3- d]pyridine ring system have been synthesized. Furo[3,4-b]indoles are synthetic equivalents to indolo-2,3-quinodimethane. Furo[3,4- b]indoles are reactive dienophiles which can provide access to carbazoles and carbolines. This methodology is investigated as a route toward carazostatin and carbazoquinocin. The Fischer indole synthesis is used to effect a convenient synthesis of 2,3'-biindoles from 3-acyl-1-(phenylsulfonyl)indoles. Both symmetrical and unsymmetrical 2,3'-biindoles are efficiently synthesized in good to excellent yields. A variety of substituent effects are demonstrated by an assortment of para -substitued hydrazines and 3-acylindoles. Various routes have been investigated for the synthesis of the biindole marine alkaloid iheyamine A. Towards this end, electron-deficient indoles are particularly useful synthons and advanced intermediates are produced via nucleophilic attack on indole.
Description	1 online resource (ix, 246 leaves) : illustrations
Format	application/pdf
Advisor	Gribble, Gordon W. ; Lipson, Jane E.G. ; Jacobi, Peter A. ; Shea, Kevin M.
Subject	Indole -- Synthesis. ; Heterocyclic compounds -- Synthesis.
College	Dartmouth College -- Department of Chemistry.
Issuing Body	Dartmouth Dissertations are made available through the Dartmouth Digital Library.
Degree	Thesis (Ph.D)--Dartmouth College.
Copyright	In Copyright. This material is protected by copyright and/or related rights. You are free to use this material in any way that is permitted by copyright law that applies to your use. For other uses, you need to obtain permission from the rights-holder(s). http://rightsstatements.org/page/InC/1.0/
DOI	https://doi.org/10.1349/ddlp.2942

Title	alford2010 1
Full Text	NUCLEOPHILIC ADDITION TO ELECTRON DEFICIENT INDOLES AND THE SYNTHESIS OF FUSED HETEROCYCLIC RING SYSTEMS A Thesis Submitted to the Faculty in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry by Philip E. Alford DARTMOUTH COLLEGE Hanover, New Hampshire December, 2010

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