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Two new methods for 2,3-pyridyne formation.

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Call No.	QD401 .S53 1996
Author	Shay, John Joseph.
Title	Two new methods for 2,3-pyridyne formation.
Date	1996
Abstract	Many alkaloids of biological importance have the 11H-pyrido (4,3,2-mn) acridine ring structure such as cystodytin and amphimedine. It would be desirable to find an effective way to synthesize a wide variety of these compounds using a single methodology. It was proposed that 4-substituted-2,3-pyridyne would be the linchpin in the synthesis of these natural products. The development of an efficient method of generating 2,3-pyridyne was necessary to employ this strategy. Two new methods of generating 4-substituted-2,3-pyridyne were developed. 4-Methoxy-2,3-pyridyne was generated from 2-chloro-4-methoxypyridine via the use of directed deprotonation. The reactive 4-methoxy-2,3-pyridyne intermediate was trapped with furan to generate 5,8-dihydro-4-methoxy-5,8-epoxyquinoline. 4-Substituted-2-trifluoromethanesulfonyl-3-trimethylsilylpyridines were used to generate 4-substituted-2,3-pyridyne by fluoride induced elimination. This methodology was utilized in the successful formation and trapping of 4-methoxy-2,3-pyridyne, 4-phenyl-2,3-pyridyne, 2,3-pyridyne, and 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-2,3-pyridyne. These reactive intermediates were trapped with furan to generate their respective 5,8-dihydro-4-substituted-epoxyquinolines. The regioselectivity of the trapping of the reactive 4-substituted-2,3-pyridyne intermediates were also studied. 2-Methylfuran was found to react in a slightly regioselective manner with 4-substituted-2,3-pyridyne to yield 8-hydro-4-substituted-5-methyl-5,8-epoxyquinoline and 5-hydro-4-substituted-8-methyl-5,8-epoxyquinoline in ratios of 4:1 to 2:1 depending on the 4-substituent. 2-Methoxyfuran, however, was found to react with 4-substituted-2,3-pyridyne to give exclusively the 5-methoxy-4-substituted-8-quinolinol regioisomer. Unsuccessful attempts to utilize this methodology in the synthesis of cystodytin and amphimedine are reported."
Description	iv, 239 leaves : ill. 28 cm
Format	application/pdf
Subject	Pyridine -- Synthesis. ; Alkaloids -- 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	All rights reserved. No part of this book may be reproduced in any form by any electronic or mechanical means without permission in writing from the author.
DOI	http://dx.doi.org/10.1349/ddlp.1805

Title	Page 1
Full Text	Two New Methods for 2^Pyridyiie Formation A Thesis Submitted to the Faculty in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry ty John Joseph Shay DARTMOUTH COLLEGE Hanover, New Hampshire August,20 1996

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Two new methods for 2,3-pyridyne formation.

Two new methods for 2,3-pyridyne formation.