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

Example text

According to (XLII) (XLIII) Sachs,& it is red while its I-methyl derivative is intensely blue, either in solution or in the solid state. A solution of naphtho [1,8]triazine in concentrated sulfuric acid is red-brown. Erdmann stated that it forms salts with acids &nd with bases; he said nothing about their stability. De Aguiar reported that salts with either acids or bases are unstable. Their decomposition is probably by way of ring opening. A German patentb* states that naphtho [1,8]triazine is extraordinarily resistant to chemical reagents in general.

55-60", said to be C,BH,,N,CI. evolves nitrogen; however, 40% of the triazine can be recovered after ten hours at 175". The product formed by this thermal decomposition, according to Shah, can have either structure XXVII or XXVIII (eq. 43). Structure XXVIII seems improbable. 3-Amino-4-oxo-3,4-dihydro-1,2,3-benzotriazine (XXIX) may have been first prepared by Finger,= who treated the hydrazide of anthranilic acid with nitrous acid to obtain a product which was not analyzed. He did not speculate on possible structures.

Thiourea. Reissert and Grube prepared S-acyl derivatives of 4-mercapto-l,2,3-benzotriazine by treating it with benzoyl chloride and sodium hydroxide or with acetic anhydride and sodium acetate. When treated with sodium and methyl iodide, 4mercapto-l,2,3-benzotriazineforms the S-methyl derivative. Alkaline permanganate converts 4-mercapto-l,2,3-benzotriazineto benzazimide, S being replaced by 0. Milder oxidizing agents would presumably convert it to its disulfide. I. 1223) is known of this type.

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