Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

Старосотников, А. М.; Lobach, A. V.; Качала, В. В.; Шевелев, С. А.

doi:10.1023/b:rucb.0000035642.41056.81

Cited by 17 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2,4,6-Trinitrobenzaldehyde, 25 disodium 5,5 0 -azotetrazolate pentahydrate, 5a diammonium (E)-1,2-bis(4-(tetrazolato)-1,2,5oxadiazol-3-yl)diazene, 7a ammonium 5-nitrotetrazolate, 4a ammonium 5-nitrotetrazolate-2N-oxide, 4d 4-amino-3-(5-tetrazolyl)furazan, 7e 2,4-dinitro-1,3-imidazole 26 and 5-nitroiminotetrazole 6h,15a were synthesized according to the literature procedures. Synthesis of N-(2,4,6-trinitrobenzylideneamino)guanidinium nitrate (1).…”

Section: Starting Materialsmentioning

confidence: 99%

Synthesis and characterization of a new family of energetic salts based on a guanidinium cation containing a picryl moiety

Wang

Yang

et al. 2015

New J. Chem.

View full text Add to dashboard Cite

A new family of energetic salts based on a new guanidinium cation containing picryl moiety, N-(2,4,6-trinitrobenzylideneamino) guanidinium cation, were synthesized and well characterized by IR and multinuclear NMR spectroscopy, differential scanning calorimetry (DSC), thermogravimetry analysis (TG) and elemental analysis. The structures of N-(2,4,6trinitrobenzylideneamino)guanidinium nitrate (1) and N-(2,4,6trinitrobenzylideneamino)guanidinium 5-nitrotetrazolate (5) were confirmed by single crystal X-ray diffraction. Most of the salts decompose at temperatures over 180 o C. Furthermore, except for salts 1 and 9, most energetic salts exhibit low impact sensitivities (20-40 J), friction sensitivities (220-340 N), and are insensitive to electrostatics. The detonation pressure values calculated for energetic salts 1 and 3-9 range from 23.7 to 30.3 GPa, and the detonation velocities range from 7842 to 8394 m s -1 . These values indicate that some energetic salts can be the candidate for energetic materials possessing good thermal stabilities and low sensitivities.

show abstract

Section: Starting Materialsmentioning

confidence: 99%

Synthesis and characterization of a new family of energetic salts based on a guanidinium cation containing a picryl moiety

Wang

Yang

et al. 2015

New J. Chem.

View full text Add to dashboard Cite

show abstract

“…The method was described for the first time by Sachs and Everding 24 and was optimized repeatedly afterwards. 25, 26 TNT reacts with p-nitrosodialkylanilines to generate nitrones 15, 27 which yield 2,4,6-trinitrobenzaldehyde 16 in the acidic hydrolysis conditions. Note that for a long time compound 15 (R=Me) was assumed to have a different structure, i.e.…”

Section: Reactions Of the Tnt Methyl Groupmentioning

confidence: 99%

“…A method for the synthesis of 1-aryl(hetaryl)-4,6-dinitro-1Н-indazoles based on 2,4,6-trinitribenzaldehyde hydrazones is described. 26,71,72 Hydrazones 71, in the presence of bases, undergo intramolecular cyclization accompanied by nucleophilic substitution of the ortho-nitro group, and indazoles 72 are produced.…”

Section: Synthesis Of Benzannelated Five-membered Heterocycles With Tmentioning

confidence: 99%

“…that of azometin 15'. [24][25][26]28 However, it has recently been established that this compound is a nitrone. The interaction of trinitrobenzaldehyde with 4-(N,N-dimethylamino)aniline has been shown to lead to compound 15' that differs from a product of TNT condensation with 4-nitroso-(N,N-dimethyl)aniline (NMR and mp data).…”

Section: Reactions Of the Tnt Methyl Groupmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Bastrakov¹,

Старосотников²,

Шевелев

2008

Arkivoc

View full text Add to dashboard Cite

Methods for the synthesis of five-membered benzannelated heterocyclic compounds from the military explosive 2,4,6-trinitrotoluene (TNT) are summarised. The general approach concerns the transformation of the TNT methyl group followed by either intramolecular substitution of the ortho-nitro group or regioselective substitution of the ortho-nitro group by an appropriate nucleophile and subsequent cyclization.

show abstract

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

et al. 2016

View full text Add to dashboard Cite

An efficient method was developed for the synthesis of 5,7-dinitroquinoline and its N-oxide. The reactions of these compounds with either thiols or sodium azide resulted in the regiospecific substitution of 5-NO 2 group and the formation of previously unknown quinoline derivatives.The 5-azido derivatives underwentr eactions with 1,3-dicarbonyl compounds and, depending on the nature of reagent, afforded either 5-(1,2,3-triazol)-1-yl-or 5-amino-7-nitroquinolines, which have been previously inaccessible by using other methods.Scheme1.Synthesis of 5,7-dinitroquinolines 1 and 2 (DMF = N,N-dimethylformamide). [a] Dr.A .M.S tarosotnikov,V .V .Nikol'skiy,A.N.B orodulya, Dr.Scheme2.Reactions of 5,7-dinitroquinolines with O-and N-nucleophiles. Scheme3.Reactions of 5,7-dinitroquinolines with thiols. Scheme4.Nucleophilic aromatic substitution of the nitro group(Nu = nuclophile).

show abstract

Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

Cited by 17 publications

References 0 publications

Synthesis and characterization of a new family of energetic salts based on a guanidinium cation containing a picryl moiety

Synthesis and characterization of a new family of energetic salts based on a guanidinium cation containing a picryl moiety

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

Contact Info

Product

Resources

About