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A. M. Starosotnikov A. V. Lobach V. V. Kachala S. A. Shevelev 《Russian Chemical Bulletin》2004,53(3):584-587
The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS– and N3
– lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4·H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring. 相似文献
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M. A. Bastrakov A. M. Starosotnikov V. V. Kachala E. N. Nesterova S. A. Shevelev 《Russian Chemical Bulletin》2007,56(8):1603-1607
Reaction of different anionic S-nucleophiles with 3-R-2-aryl-4,6-dinitroindoles led to a regiospecific nucleophilic substitution
of the nitro group in position 4 with 6-NO2 group remaining intact. The representatives of some peri-annulated polycyclic systems were synthesized on the basis of the substitution products.
Dedicated to Academician V. A. Tartakovsky in honor of his 75th anniversary.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1543–1547, August, 2007. 相似文献
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Vinogradov V. M. Dalinger I. L. Starosotnikov A. M. Shevelev S. A. 《Russian Chemical Bulletin》2001,50(3):464-469
A new procedure was developed for the preparation of 4,6-dinitro-3-R-benzo[d]isoxazoles (R are derivatives of the aldehyde group) based on 2,4,6-trinitrophenylacetaldehyde. The resulting compounds are characterized by the regiospecific substitution of the nitro group at position 4 under the action of anionic nucleophiles RS–, RO–, F–, or N3
–, which allowed the development of a new method for the preparation of previously unknown 4-Nu-6-nitro-3-R-benzo[d]isoxazoles (Nu is the residue of a nucleophile). At the same time, oxidative nucleophilic substitution under the action of anions of some -dicarbonyl compounds leads to the replacement of the hydrogen atom at position 7 with the corresponding C-nucleophiles. 相似文献
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Starosotnikov A. M. Vinogradov V. M. Kachala V. V. Shevelev S. A. 《Russian Chemical Bulletin》2002,51(8):1519-1522
The previously unknown recyclization of nitrobenzo[d]isoxazoles into 1,2,3-triazoles was found. A general method for the synthesis of 2-aryl-4-(2-hydroxy-4-nitro-6-R-phenyl)-1,2,3-triazoles from 4-R-6-nitrobenzo[d]isoxazole-3-carbaldehyde arylhydrazones was developed. 相似文献
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M. A. Bastrakov A. M. Starosotnikov A. Kh. Shakhnes S. A. Shevelev 《Russian Chemical Bulletin》2008,57(7):1539-1542
Transformation of the amino group in 7-amino-1-methyl-4,6-dinitro-2-phenylindole afforded a number of new 7-R-4,6-dinitroindoles
and a first representative of a novel tricyclic heteroaromatic system of [1,2,5]oxadiazolo[4,3-g]indole.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1508–1511, July, 2008. 相似文献
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