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  • About
  • The Global ETD Search service is a free service for researchers to find electronic theses and dissertations. This service is provided by the Networked Digital Library of Theses and Dissertations.
    Our metadata is collected from universities around the world. If you manage a university/consortium/country archive and want to be added, details can be found on the NDLTD website.
1

Further studies of the reactions of quinoxaline and 2-methylquinoxaline

Myers, Marcus N. 02 April 1952 (has links)
The present investigation was also made with the object of preparing the vinylquinoxalines and studying their 1,4- addition reactions. The attempts to prepare vinylquinoxalines were unsuccessful. However, sodium acetylide reacted with 2,3-dichloroquinoxaline to give a new compound which (from its analysis and properties) appears to be 2,3-bis(1-hydroxyethyl) quinoxaline . This new compound should be investigated further , as it may prove to be an intermediate in the preparation of vinylquinoxalines. The preparation of 2-methylquinoxaline has become very simple by the use of the method of Jones, Kornfeld and McLaughlin^5, which consists of condensing o-phenylenediamine with pyruvic aldehyde. The condensation of chloral with 2-methylquinoxaline by the method of Jones^5 was repeated to obtain 2-(3,3,3-trichloro-1- propenyl)quinoxaline. Attempts to dehydrohalogenate the latter compound with palladium on barium sulfate as a catalyst resulted in a new compound, as yet unidentified, when triethylamine was also present. The hydrolysis of 2-(3,3,3-trichloro-1-propenyl)quinoxaline with sodium hydroxide was accomplished, giving β-(2-quinoxalyl)acrylic acid. Attempts made to decurboxylate β-(2-quinoxalyl)acrylic acid by various methods were unsuccessful; however o-phenylenodiamine was obtained using a concentrated sodium hydroxide solution for decarboxylation. The β-(2-quinoxalyl)acrylic acid was also brominated, and attempts made to decarboxylate the α,β-dibromo- (2-quinoxalyl)propionic acid were unsuccessful. Attempts to accomplish an anil addition of sodium phenylacetylide to quinoxaline and 2-methylquinoxaline were unsuccessful. A new unidentified compound was obtained on treating β-(2-quinoxalyl)acrylic acid in methanol with hydrogen chloride. The spectrophotometric data in the ultraviolet range were obtained on pyridine , α-picoline, 2-vinylpyridine, 2-methylquinoxaline, quinoxaline , and an unknown compound of quinoxaline which was proved to be 2-methylquinoxaline.

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