Chemistry of Heterocyclic Compounds: The 1,2,3- and by John G. Erickson

By John G. Erickson

Content material:
Chapter I The 1,2,3?Triazines (pages 1–43): John J. Erickson
Chapter II The 1,2,4?Triazines (pages 44–137): John J. Erickson
Chapter III The 1,2,3,4?Tetrazines (pages 138–176): V. P. Wystrach
Chapter IV The 1,2,3,5?Tetrazines (pages 177–178): John J. Erickson
Chapter V The 1,2,4,5?Tetrazines (pages 179–249): Poul F. Wiley
Chapter VI The Pentazines (pages 250–251): John J. Erickson

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Additional resources for Chemistry of Heterocyclic Compounds: The 1,2,3- and 1,2,4-Triazines, Tetrazines & Pentazines, Volume 10

Sample text

3). This type of reaction has apparently not been explored with aliphatic hydrazidines. Pinner,u6 however, attempted to prepare S-phenyl-astriazine from glyoxal and benzhydrazidine. Instead of the desired product, he obtained an osazone-like compound (eq. 4). It appears to us NH2 I C&H,C= NNH, I CHOCHO ____). CeH&=NN=CH I C,H,C=NN=CH (4) that by proper choice of experimental conditions the reaction might be made to follow the desired course. Perhaps, in very dilute solutions, one molecule of benzhydrazidine could react with one of glyoxal and then cyclize to 3-phenyl-us-triazine before the reaction to form the osazone took place.

The last name, of course, does not uniquely specify the structure. A solitary compound of this type is known. It was prepared by Fries, Walter, and Schillings' by treating 3-aminonaphthalene-2carboxamide or 3-aminonaphthalene-2-carbohydrazidewith nitrous acid (eq. 57). The yield of product is apparently very good. p. ), soluble in strong alkali and in acetic acid, less soluble in dioxane and acetone. When heated with resorcinol, it forms a red am dyestuff. I. 1822). In 1874 de Aguiarzz prepared the first 1,2,3-triazine known.

It is named triazirinoindiazole by TheRing Index. Other names that have been used are trim’rimindiazene, cycloazibenztriaziw, and endoiminodihydrobenzisodiazole. H H Triazirinoindiazole Chattaway and Walkeru observed that bromination or chlorination of o-nitrobenzylidenephenylhydrazonesyield so-called o-halogen derivatives (XXXVI). These explosive compounds were at first designated as substituted “isodiazomethanes” (XXXVII) (eq. 54). These reactions are illustrated by the bromination of o-nitrobenzylidenephenylhydrazone.

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