Arylazoglyoxalinecarboxylic acids / by Robert George Fargher.

  • Fargher, Robert George.
Date:
1921.]
Catalogue details

Licence: Public Domain Mark

Credit: Arylazoglyoxalinecarboxylic acids / by Robert George Fargher. Source: Wellcome Collection.

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    XVII.—Arylazoglyoxalinecarboxylic Acids. By Robert George Fargher. Arylazoglyoxalinecarboxylic acids have been prepared by Burian (2?er., 1904, 37, 696) by the interaction of sodium diazo- benzene-p-sulphonate and glyoxaline-4:5-dicarboxylic acid or its 2-methyl or 2-phenyl homologues. Although the reaction involved the loss of carbon dioxide, he assumed the products to be A-aryl- azo-derivatives. Since then (T., 1919, 115, 217, 1415; 1920, 117, 668), it has been shown that the arylazoglyoxalines are (7-azo- and not A-azo-derivatives, and that the product of the reaction between sodium glyoxalinedicarboxylate and sodium diazobenzene -p - sulphonate is 2-p-sulphobenzeneazoglyoxaline-4 : 5-dicarboxylic acid, and not l-p-sulphobenzeneazoglyoxaline-4-carboxylic acid, as stated by Burian. Nevertheless, combination is accompanied to some extent by loss of carbon dioxide, as quantitative experiments with both glyoxalinedicarboxylic acid and its 2-methyl derivative showed, and, in view of the importance of the 4-arylazoglyoxaline- 5-carboxylic acids as intermediate compounds in the synthesis of the purine ring from the glyoxaline nucleus, the reaction has now been submitted to further examination. p-Bromobenzenediazonium chloride combines readily with 2-phenylglvoxaline-4:5-dicarboxylic acid in sodium carbonate solu-