Hydrazine 1,2-diformyl

Triazole has been prepared by the oxidation of substituted 1,2,4-triazoles, by the treatment of urazole with phosphorus pentasulfide, by heating equimolar quantities of formyl-hydrazine and formamide, by removal of the amino function of 4-amino-l,2,4-triazole, by oxidation of l,2,4-triazole-3(5)-thiol with hydrogen peroxide, by decarboxylation of 1,2,4-triazole-3(5)-carboxylic acid, by heating hydrazine salts with form-amide,by rapidly distilling hydrazine hydrate mixed with two molar equivalents of formamide, i by heating N,N -diformyl-hydrazine with excess ammonia in an autoclave at 200° for 24 hours, and by the reaction of 1,3,5-triazine and hydrazine monohydrochloride. ... 

Can be prepd by the nitration of 1-phenyltetrazole with fuming nitric acid, or by heating sym diformyl-hydrazine, OHC.HN.NH.CHO, and p-nitrobenzene-diazonium chloride, 02N.C6H4.N2C1, with dil Na hydroxide soln. Insol in w and ligr, diff sol in benz and eth, sol in ethanol and methanol, v sol in acet. Puffs off when heated above its mp Refs 1) Beil 26, 347 (109) 2)M. Freund ... 

Nieht reduzierbar sind l,l-Dialkyl-2-benzoyl-hydrazine und 1,2-Diformyl-hydrazin. 

Analog erhalt man aus Trimethyl-formyl-hydrazin Tetramethyl-hydrazin (55% d.Th. Kp 71-72°). Die Reduktion von l,2-Dimethyl-l,2-diformyl-hydrazin ergibt nur 15% d.Th. Tetramethyl-hydrazin5 (zur Arbeitsvorschrift s. ds. Handb., Bd. X/2, S. 50). 

Disubstituted tetrazoles are conveniently prepared from acyl hydrazines (98) and diazonium salts.166 The reaction proceeds through the intermediate tetrazenes (99) followed by cyclization to the tetrazole (100) (Scheme 13). The intermediate can be isolated under mildly basic conditions. Symmetrically 1,2-diacylated hydrazines yield 1-substituted tetrazoles through the elimination of one of the acyl groups.166 - 168 Diformyl-hydrazine is a very convenient starting material for 1-substituted tetrazoles.166, Unsymmetrically 1,2-diacylated hydrazine usually results in mixtures.169... 

Amino-1,2,4-triazole has been obtained from orthoformic ester and hydrazine hydrate in a sealed tube at 120° 1 by heating formylhydrazine at 150-210° 2-3-4 by heating N,N -diformyl-hydrazine at 160° 5 by decarboxylation of 4-amino-1,2,4-tria-zoldicarboxylic acid 6 by fusion of l,2-dihydro-l,2,4,5-tetrazine 6 and by heating l,2-dihydro-l,2,4,5-tetrazinedicarboxylic add above its melting point.4-6-7... 

Mit Arylhydrazinen reagiert 2,2 -Diformyl-biphenyl zu 9-Arylazo-phenanthrenen, die durch Kondensation von Nitroso-benzolen mit 9-Amino-phenanthren nicht zuganglich sind (2,2 -Diformyl-biphenyl kann mittels Ozonolyse von Phenanthren in 65-85% Aus-beute hergestellt werden). Die Ausbeuten sind hoch (60-90%)3. Es ist moglich, anstelle der freien Hydrazine auch die Hydrochloride einzusetzen ... 

The reaction of both aldehydic groups in 3,5-diformyl-4-ethyl-4//-pyran (85b) and in analogous 4//-thiopyrans 38b and 339 with a carbocyclic Wittig reagent was successfully explored in the syntheses of hetero[17]annulene 608 (Scheme 37).85 Analogous 3,5-diformyl derivative 85d reacted with phenyl-hydrazines to give Schiff bases 609.418 Hydroxylamine and 85d at room... 

The complexes ML2-nH20 (M = Zn or Cd H2L = diformyl- or diacetyl-hydrazine) have also been synthesized, and are dimeric or polymeric with the quadridentate hydrazine acting as a bridging ligand.158 159 A normal coordinate analysis of diformylhydrazine and its zinc complex with deprotonated ligand has been reported.160... 

Diformyl-2,5-diphenyltellurophene and hydrazine hydrate condensed in absolute methanol at 20° to give 5,7-ciiphenyItelluropheno[3,4-d pyridazine2. 

A final example of a bipyrrole-derived [2 + 2] Schiff base expanded porphyrin was reported by Johnson, et al. in 1995 in the form of a preliminary abstract. In this instance, macrocycle 9.34 was prepared via the condensation of hydrazine with the diformyl bipyrrole 9.23 (Scheme 9.1.6). This macrocycle was reported to exhibit spectral characteristics indicating that it is antiaromatic. Further, treatment with manganese dioxide was said to result in oxidation of 9.34 to an aromatic 22 7t-electron system. This latter system proved, however, to be much less stable than its 24 7i-electron parent , and this precluded isolation and characterization. In fact, with full experimental details not yet reported in the literature, the characterization, and structural assignment for 9.34 must also be considered tentative. 

The base-catalyzed additions of glyoxal to formamide and methanesulfonamide afforded 1,4-diformyl- (895, 1663) and l,4-bis(methylsulfonyl) derivatives (895) of 2,3,5,6-tetrahydroxypiperazines, respectively, in addition to the corresponding A iV -disubstituted 1,2-diamino-l, 2-ethanediols (895). Salts of 2,3,5,6-tetrahydroxy-piperazine-l,4-disulfonic acid were similarly prepared by the addition of aqueous glyoxal to sulfamic acid in the presence of base (1664). Ethylene dichloride with hydrazine in ethanol gave ethylene dihydrazine, 1,4-diaminopiperazine, and poly(ethylenehydrazine) (1665). 

Diformyl-3-ethinyl-pentandial und Hydrazin bzw. Aryl-hydrazine bilden 3,3-Bis-[lH-pyrazol-4-yl]-propine200 ... 

Dipyrazolyl steroids (242 X = NH)and(244 X = NH) have been obtained by the reaction of the 2,6- and 4,6-diformyl compounds (241) and (243) with hydrazine whilst similar condensation with the unsaturated keto-aldehyde derived from (221) gives the pyridazine (245). 

Formyl hydrazine (formic acid hydrazide) [624-84-0] M 60.1, m 54 , 54-57 , pKest 2.5. Reciystalhse it from EtOH and dry it in vacuo. Store below 10° it may disproportionate on storage to 1,2-diformyl hydrazine and hydrazine. It forms a blue [Cu(CH4N20)]S04 salt with CUSO4. [Beilstein 2 H 93, 2 111 127, 2IV 85.]... 

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