Further studies of the reactions of quinoxaline and 2-methylquinoxaline
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.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Myers, Marcus N., "Further studies of the reactions of quinoxaline and 2-methylquinoxaline" (1952). Theses and Dissertations. 8313.