Nitroazines. 3. Nitroacetonitrile in the synthesis of nitroazines

Русинов, В. Л.; Petrov, Alexander Yu.; Чупахин, О. Н.; Klyuev, N. A.; Александров, Г. Г.

doi:10.1007/bf00506077

Cited by 19 publications

(18 citation statements)

References 7 publications

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“…We think that the mechanism is similar to that of the cyclization described in the monograph [48], with an intermediate formation of an isoxazole derivative. …”

mentioning

confidence: 79%

Transformations of 5‐nitropyrimidines

Riabova

Makarov

Граник

et al. 2008

Journal of Heterocyclic Chem

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“…We think that the mechanism is similar to that of the cyclization described in the monograph [48], with an intermediate formation of an isoxazole derivative. …”

mentioning

confidence: 79%

Transformations of 5‐nitropyrimidines

Riabova

Makarov

Граник

et al. 2008

Journal of Heterocyclic Chem

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“…Also spectra of 1,2,4-triazine derivatives 14*, 15* was characterized by 13 ]triazin-7-one derivative 4'a* (Scheme 5) according to the procedures described earlier for unlabeled compounds [14][15][16][17][18][19] . We synthesized [ 15 N]-labeled 5-amino-1,2,4-triazole 1a* starting from guanidine sulfate 16 and using enriched K 15 NO 2 (86% of 15 N) (Scheme 4).…”

Section: Methodsmentioning

confidence: 99%

The synthesis of labeling azolo-1,2,4-triazines with 15N isotope in azole and azine parts

Шестакова¹,

Деев²,

Ulomskii³

et al. 2008

Arkivoc

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“…Seriya Khimicheskaya, No. 3 (2) 5959 (7) 16015 (25) 5762 (13) 61(2) C (3) 6348 (6) 14613 (23) 6183 (9) 34(2) C (4) 6714 (7) 13954 (19) 5610 (10) 32(2) C(4A) 6640 (7) 14438 (22) 4527 (10) 41(2) C (10) 6979 (8) 13373 (21) 3922 (11) 42(2) C(5A) 7149 (7) 14666 (21) 3235 (10) 39(2) C (5) 7778 (5) 14506 (23) 2932 (8) 39(2) C (6) 7955 (9) 15681 (23) 2184 (13) 49(2) C (7) 7534 (5) 16910 (21) 1787 (9) 20(2) C (8) 6912 (7) 16730 (26) 1966 (10) 55 (2) …”

Section: 3unclassified

Molecular and electronic structures and conformational analysis of derivatives of 9-nitroanthracene, anionic σ-complexes

et al. 1998

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Potassium 10-methoxy-9-nitroanthracenide was studied by X-ray diffraction analysis. The central ring of the anthracene fragment adopts an asymmetrically flattened boat conformation. The bond lengths in the C(Ar)--C(NO2)--C(Ar) fragment are indicative of the presence of conjugation between the 7t-systems of the benzene rings and the nitro group owing to a substantial contribution of the aci form to the structure of the nitro group.Quantum-chemical calculations of anionic cr-complexes of 9-nitroanthracene derivatives were performed. In all cases, the central ring adopts two conformations with the pseudoaxial and pseudoequatoria[ orientations of the substituents at the saturated C(10) atom, respectively. The relative stability of the conformers and the factors determining the stability were considered. The minima on the potential energy surface have a flattened shape in spite of relatively high barriers to the conformational transition (2--4 kcal tool-l). The deviation of the C(Ar)--C(Ar)--C(sp3)--C(Ar) torsion angle from the equilibrium value by +20 ~ causes an increase in the energy of the anion by less than 1 kcal tool -I. The effect of the substituents oll the charge distribution was considered.Key words: 9-nitroanthracene, anionic <~-complexes, molecular structure, conformational analysis, X-ray diffraction analysis, semiempirical quantum-chemical AM1 method.Anionic c~-complexes of aromatic polynitro compounds are intermediates in reactions of nucleophilic substitution, l Studies of the spatial structures of these compounds can provide important data on the reactivity and fine details of the reaction mechanisms. Unfortunately, because of the instability of or-complexes, it is generally not only difficult to study them by X-ray diffraction analysis but even impossible to isolate these compounds from solutions. Because of this, experimental data z-s on the structures of these compounds are scarce.The aim of this work is to theoretically and experimentally study the molecular and electronic structures of anionic G-complexes of 9-nitroanthracene 1--3. 2 3Experimental Potassium salt of anion 2 was prepared according to a procedure reported previously. 9 Crystals were grown by slow cooling of a solution of the salt in methanol.X-ray diffraction analysis. Crystals of the salt 2-K +-5MeOH-3H20 are monoclinic. At -80 ~ a = 21.398(8) A, b = 7.564(3) A, c = 13.295(5) A, 13 = 107.21(3)% V = 2056(3) A 3, space group C2, Z = 4, de.ale = 1.342 gcm -3, /~ = 0.295 mm -t. Intensities of 1900 independent reflections (Pin ~ = 0.08) were measured on a four-circle automated Syntex P21/PC diffractometer (graphite monoehromator, Mo-Kct radiation, 0/20 scanning technique, 20max = 50*). We carried out the profile analysis of the X-ray diffraction data according to a known procedure, 10 which made it possible to improve substantially the quality of the data set.The structure was solved by the direct method with the use of the SHELXTL PLUS 4.2 program package. 11 The positions of the hydrogen atoms of the anthracene fragment were calculat...

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Nitroazines. 3. Nitroacetonitrile in the synthesis of nitroazines

Cited by 19 publications

References 7 publications

Transformations of 5‐nitropyrimidines

Transformations of 5‐nitropyrimidines

The synthesis of labeling azolo-1,2,4-triazines with 15N isotope in azole and azine parts

Molecular and electronic structures and conformational analysis of derivatives of 9-nitroanthracene, anionic σ-complexes

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