3- Hydrazino-5,6-diphenyl triazine

The synthesis of the triazinotriazines 519 was achieved (87MI5) by reaction of 3-hydrazino-5,6-diphenyl[l,2,4]triazine 518 with 4-substituted phenacyl halides. These triazinotriazines were screened against P-388 lymphocytic leukemia in mice and were inactive. 

Thus, 5-aryl-3-hydrazino[l,2,4]triazine 200 was reacted with acid chlorides to yield 201 <2004AF42>, and reaction of 5,6-diphenyl-3-hydrazino[l,2,4]triazine 202 with carbon disulfide yielded a 3-mercapto product 203 <2000PJS214>. 

Also in the mass spectrum of 3-hydrazino-5,6-diphenyl-l,2,4-triazine (82) the elimination of nitrogen from the molecular ion could not be detected. The dominant process in this case is the fragmentation of the molecular ion into a highly delocalized diphenylacetylene radical ion at 178 mass units (7lOMS(5)i085). 

Treatment of 3-amino-5-hydrazino-l,2,4-triazole with benzil produced 2-amino-6,7-diphenyl-[l,2,4]triazolo[5,l-c][l,2,4]triazine via either direct formation involving cycliz-ation on the triazole N-1 or attack at N-4 of the triazole to yield the [3,4-c] compound which rearranged to the [5,1-c] isomer (76JCS(P1)1492). Ring closure of 3,4-diamino-1,2,4-triazines with carboxylic acids is also a route to various [l,2,4]triazolo[5,l-c][l,2,4]triazines (64CB2173). 

Cyanopyrazine with dicyanodiamide [(NH2CN)2] gave the 2-(4, 6 -diamino-triazin-2 -yl)pyrazine (63), with o-phenylenediamine in the presence of poly-phosphoric acid at 250 gave 2-(benzimidazol-2 -yl)pyrazine, and with hydrazine gave 2-(C-hydrazino-C-iminomethyl)pyrazine, which condensed with benzil to 2-(5, 6 -diphenyl-as-triazin-3 -yl)pyrazine (64) (1441). 

IIydrazino-5,6-diphenyl-l,2,4-triazine reacts with 4-arylidene-2-phenyloxazol-5(4//)-ones and 4-benzylidene-3-methylisoxazol-5(4//)-ones in toluene to afford products 19 and 20, respectively, substituted in the hydrazino group.299... 

The IR spectra of Co(ll,lll) and Cu(ii) complexes of hydrazones obtained by the reaction of 5,6-diphenyl-3-hydrazino-l,2,4-triazine with furfural <2002TML398> and 2-acetylpyridine <2004JCR105> have been studied to determine the coordination sites of these ligands. In addition, Mn(ii), Ni(ii), and Cu(ll) complexes of hydrazones derived from 4-amino-3-mercapto-6-methyl-l,2,4-triazin-5(4//)-one were elucidated by IR spectra <2000SRI979>. 

---