3.5- Dinitro-2- pyridine

Bis (picryl amino)-3,5-dinitro pyridine (PYX) 460 1.75 63 7450 Slightly impact sensitive. Regarded as a substitute for HNS. Used for thermally stable perforators for oil and gas wells. 

Hydroxy-dinitro pyridines, e.g., act as electron acceptors and/or as proton donors to, e.g., napthalene derivatives. 

Dimethylamino-3,5-dinitropyridine is obtained from 2-chloro-3,5-dinitro-pyridine with 40% aqueous dimethylamine. 2-Diethylamino-3,5-dinitropyridine is formed from anhydrous diethylamine and 2-( 3-chloroethoxy)-3,5-dinitropyii-dine. ... 

Amino acids and peptides can be reacted with 2-chloro-3,5-dinitro-pyridine like with l-fluoro-2,4-dinitrobenzene. Terminal substituted... 

When pyridine 1-oxide reacts with bromine, sodium acetate and acetic anhydride, 3,5-dibromopyridine 1-oxide is formed . / -Nitrobenzoyl chloride and silver nitrate produce small yields of 3-nitro- and 3,5-dinitro-pyridine l-oxide . These reactions probably involve nucleophilic addition, followed by electrophilic substitution, and the first step can be represented as occurring at C(4), though not with any compelling reason ... 

Dinitrothiobenzoates. Mercaptans react with 3 5-dinitro-benzoyl chloride in the presence of pyridine as a catalyst to yield 3 5-di-nitrothiobenzoates ... 

Pyridine, 2-(dimethylamino)-5-nitro-nitration, 2, 189 Pyridine, 3,5-dinitro-conformation, 2, 110 Pyridine, 3,5-diphenyl-synthesis, 2, 0... 

In 2-substituted dinitrothiophenes, phenylsulfone and p-nitro-phenoxy groups both react faster than the chloro group with pyridine, i.e., in a reverse order with respect to l-substituted-2,4-dinitro-benzenes, although with both substrates the factors involved are small. 

The dinitro derivative of compound 2 reacts with anhydro bases of pyridine and quinoline to give zwitterions such as 215 (99RCB1391). Compound 216 has been made from the 3-bromo derivative of compound 3 by reaction with an amine, as an intermediate in the production of stomach secretion inhibitors (80EUP48555),... 

Excellent yields of the oximes of phenylacetaldehydes are obtained by reduction of 6-nitrostyrenes over Pd-on-C in a pyridine solvent (74,75). The technique gives yields of only about 60% when applied to aliphatic unsaturated nitrocompounds better yields are obtained in acidic media(6 5). Over 5% Rh-on-Al203 in ethanol-acetic acid-ethyl acetate, 2- 6-dinitro-styrenes are converted to 2-nitrophenylacetaldehyde oximes (13). 

Dinitronaphthalene ( Gamma-dinitronaph-thalene, 1,3-DNN), Bright yel needles from aq pyridine, mp 144°, bp subl (Refs 1 32) CA Registry No 606-37-1. It is prepd by the action of nitric ac/sulfuric ac on naphthalene at low temps (Refs 14 33) by the nitration of 1-MNN with a mixt of 17.3% nitric ac, 61.2% sulfuric ac, and 21.5% w, temp 59-75°, time 90min (Ref 52) by the action of powd Cu (Ref 18) or hydrazine (Ref 22) on l-chioro-2,4-dinitro-naphthalene by the diazotization of 2,4-dinitro-1-naphthylamine followed by redn of the dia-zonium salt with EtOH (Ref 25) or by the action of Br on 5,7-dinitro-l,2,3,4-tetrahydro-naphthalene followed by dehydrobromination (Ref 13). It is used to prep more highly nitrated naphthalenes... 

Dinitro-6-methylamino-l,2,3,4-tctrahydro-aus 3,5-Dinitro-2-methylamino-pyridin und Natriumboranat, danach SalzsauTe 90... 

Nitroenamines and related compounds have been used for synthesis of a variety of heterocyclic compounds. Rajappahas summarized the chemistry of nitroenamines (see Section 4.2).140 Ariga and coworkers have developed the synthesis of heterocycles based on the reaction of nitropyridones or nitropyrimidinone with nucleophiles. For example, 2-substituted 3-nitro-pyridines are obtained by the reaction of l-methyl-3,5-dinitro-2-pyridones with ketones in the presence of ammonia (Eq. 10.82).141... 

Axenrod and co-workers reported a synthesis of TNAZ (18) starting from 3-amino-l,2-propanediol (28). Treatment of (28) with two equivalents of p-toluenesulfonyl chloride in the presence of pyridine yields the ditosylate (29), which on further protection as a TBS derivative, followed by treatment with lithium hydride in THF, induces ring closure to the azetidine (31) in excellent yield. Removal of the TBS protecting group from (31) with acetic acid at elevated temperature is followed by oxidation of the alcohol (32) to the ketone (33). Treatment of the ketone (33) with hydroxylamine hydrochloride in aqueous sodium acetate yields the oxime (34). The synthesis of TNAZ (18) is completed on treatment of the oxime (34) with pure nitric acid in methylene chloride, a reaction leading to oxidation-nitration of the oxime group to em-dinitro functionality and nitrolysis of the A-tosyl bond. This synthesis provides TNAZ in yields of 17-21 % over the seven steps. 

The fused pyridine-furoxan (74) has been synthesized from 3,5-dinitro-2-chloropyridine (72) via the azide (73)." ... 

PADP (171), an explosive synthesized from the reaction of 3,5-dinitro-2,6-bis-(hydrazino)pyridine with picryl chloride in DMF followed by oxidation with nitric acid, also exhibits high thermal stability. 2,4,6-Tris(picrylamino)-3,5-dinitropyridine (172) exhibits much lower thermal stability than both PYX (170) and PADP (171), a consequence of increased steric crowding around the pyridine ring. ° ... 

Dinitro-2-(picrylazo)pyridine, 3387 l-(3,5-Dinitro-2-pyridyl)-2-picrylhydrazine, 3389... 

Several of the methods of synthesis of 2,2 -bipyridines have their counterpart in the preparation of 4,4 -bipyridine. The Ullmann reaction has been used to prepare 4,4 -bipyridine. Thus 4-halogenated pyridines afford 4,4 -bipyridine. Dehalogenation and dimerization of 4-bromopyridine may be accomplished too with hydrazine and alkali at 65°C in the presence of a palladium catalyst, whereas 4-chloropyridine is converted to 4,4 -bipyridine in 46% yield by reaction with alkaline sodium formate in the presence of palladium on charcoal and a surfactant. Several extensions of the Ullmann reaction have recently been reported, especially for the synthesis of substituted 4,4 -bipyridines. Thus 4-iodo-2-methylpyridine gives 2,2 -dimethyl-4,4 -bipyridine, 3-nitro-4-chloropyridine affords 3,3 -dinitro-4,4 -bipyridine, 4-bromo- or 4-iodotetrafluoropyridine gives octafluoro-4,4 -bipyridine, and 4-iodo- or 4-bromotetrachloropyridine gives octachloro-4,4 -bipyridine. Related syntheses have been de-... 

Reaction of 3,5-dinitro-4-hydroxyaminopyridine with picryl chloride in the presence of base affords the oxadiazolo-pyridine 22 and picric acid (Equation 14) <2000CHE1003>. 

Dipyridyl-hydrazine lassen sich aus 3,5-Dinitro-pyridinen und Hydrazin gewinnen. Hierbei entsteht je nach den Reaktionsbedingungen 3,5-Dinitro-2-hydrazino-pyridin oder... 

Bis-[3,5-dinitro-2-pyridyl]-hydrazin. Mit2-Chlor-l,3,5-trinitro-benzol konnen Hydra-zino-pyridine aryliert werden. Alle Verbindungen bilden unter Einwirkung von rauchender Salpetersaure die hochcxplosiven Azo-Verbindungen6 ... 

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