The Reaction of Cyanogen with Organic Compounds. IV. Aminopyridines

Abstract

1. Cyanogen reacts with neutral aqueous solutions of certain 2-aminopyridinee to give N-(pyridyl-2) cyanof ormamidines.2. Under proper conditions cyanogen reacts with certain 2-aminopyridinee to give N ,N'-di-(pyridyl-2)oxamidines.3. N-(pyridyl-2) cyanoformamidine has been made to react with 2-aminopyridine to give N,N'-di-(pyridyl-2)oxamidine.4. N -(pyridyl-2) cyanof ormamidines hydrate rapidly in acid solution to give C-carbamylformamidines.5. The isolation of the cyanof ormamidines and the conversion of a cyanoformamidine to an oxamidine is the first direct evidence for the existence of cyanoformamidines as intermediates in the reaction of cyanogen with primary amines.

The Synthesis And Chemistry Of Cyanogen

“…Aromatic amines and ammonia were found by earlier workers to react readily with cyanogen to give oxamidines and numerous unidentified by-products, the identities of which have still not been determined. The reactions of aliphatic and heterocyclic amines with cyanogen, which had not been reported prior to 1950, have recently been studied in a comprehensive manner by Woodburn and associates (215,216,218,219,221,222).…”

“…These bispyridyloxamidines can also be obtained from pyridylcyanoformamidines and aminopyridines. The pyridylcyanoformamidines can be converted into carbamylformamidines (XI) (table 8) on reaction with hydrochloric acid followed by neutralization with ammonium hydroxide (222). 9).…”

THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS. VII. GRIGNARD REAGENTS1

“…Cyanogen was prepared by the reaction of aqueous sodium cyanide with a boiling solution of cupric sulfate and was purified as previously described (6). When used in solution it was dissolved in dry ether at -5°.…”

THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS. V. MERCAPTANS1,2

“…erty of organic substances reacting with cyanogen (6) it was of interest to work with mercaptans of varying acidity. Accordingly, not only a series of aliphatic mercaptans, but also thiophenol, certain para-substituted thiophenols (chloro, methyl, and nitro), and thiophenethiol were investigated.…”