Guanyl aminotetrazole

When 5-ATZ was treated with freshly redistilled benzaldehyde(instead of acetaldehyde), the resulting mixt consisted of crysts explg at 183°, which proved to be guanyl-aminotetrazGle together with some guanyl-aminotetrazole nitrate and some unreacted 5-aminotetrazole... 

The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of excess acetic acid produces 1,3-ditetrazolyltriazine (89), another nitrogen-rich heterocycle (C2H3N11 = 85 % N) which readily forms explosive metal salts. The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of mineral acid yields guanyl azide (90), of which, the perchlorate and picrate salts are primary explosives. Guanyl azide (90) reacts with sodium hydroxide to form sodium azide, whereas reaction with weak base or acid forms 5-aminotetrazole. ... 

Guanyl azide is then isomerized to aminotetrazole (V) which undergoes diazo-tization and couples with aminoguanidine as stated above. 

This substance forms salts with acids, and was first isolated in the form of its nitrate. The nitrate is not detonated by shock but undergoes a rapid decomposition with the production of light when it is heated. The picrate and the perchlorate explode violently from heat and from shock. Guanyl azide is not decomposed by boiling water. On hydrolysis with strong alkali, it yields the alkali metal salt of hydrazoic acid. It is hydrolyzed by am-moniacal silver nitrate in the cold with the formation of silver azide which remains in solution and of silver cyanamide which appears as a yellow precipitate. By treatment with acids or weak bases it is converted into 5-aminotetrazole. 

R. Bird A.J. Power. Thermal Decomposition of Tetrazene at 90°C , MRL-R-710, Australia (1978) [The authors report that Tetrazene is converted into 5-aminotetrazole in less than three days at 90°, thus losing its stab sensy property. Spectroscopic evidence indicates that the 5-aminotetrazole is derived from both the side chain (via guanyl azide) and the Tetrazole ring] 24) G.B. Franklin C.F. Parrish, Radiation Polymerized Priming Compositions , USP 4056416 (1977) CA 88, 52661 (1978) [The inventors claim that extrudable primers with good percussion sensy are prepd from Tetrazene 3.9—4.1, n-Pb Styphnate 32—42,... 

A series of 5-aminoaryltetrazoles were obtained directly from the corresponding l-aryl-5-aminotetrazoles by a one-pot sequential ring-opening, azidation, and intramolecular cyclization. 5-Alkylamino-l-aryltetrazoles are formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. The influence of the aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of the intermediate guanyl azides was revealed <2006S1307>. 

Alkylamino- or 5-arylaminotetrazoles can be equilibrated with 1-alkyl or l-aryl-5-aminotetrazoles respectively. Lieber has shown that tiiis isomerization goes through the corresponding guanyl azides, rather than through bicyclic intermediates discussed earlier... 

An tmino-dcrivative of carbamoyl azides, guanyl azide can react forming 5- aminotetrazol (X) (73), a substance with explosive properties ... 

In a similar way to azidoazomethines, the corresponding azido oximes and hydrazides may be obtained (Scheme 43). The formation of cyclic tautomers seems to play only a minor role here." The stereochemical aspects of the transformation of 0-acylhydroxamoyl chlorides (33 R = "Ac) with N3 ions have been studied by Hegarty. Further systems such as the interesting pairs guanyl azides (34)/5-aminotetrazoles, are comprehensively discussed by Lwowski. ... 

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