Selective synthesis and structure of highly functionalised ethylideneindolinone
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2019-04-21 12:30
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ZVEAGHINŢEVA, Marina; SUCMAN, Natalia; STINGACI, Eugenia; KRAVTSOV, Viktor; MACAEV, Fliur. Selective synthesis and structure of highly functionalised ethylideneindolinone. In: Materials Science and Condensed Matter Physics. Ediția a 9-a, 25-28 septembrie 2018, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2018, p. 160.
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Materials Science and Condensed Matter Physics
Ediția a 9-a, 2018
Conferința "International Conference on Materials Science and Condensed Matter Physics"
Chișinău, Moldova, 25-28 septembrie 2018

Selective synthesis and structure of highly functionalised ethylideneindolinone


Pag. 160-160

Zveaghinţeva Marina1, Sucman Natalia1, Stingaci Eugenia1, Kravtsov Viktor2, Macaev Fliur1
 
1 Institute of Chemistry,
2 Institute of Applied Physics
 
Disponibil în IBN: 6 februarie 2019


Rezumat

Indolinones appear in a large variety of structures of both natural and unnatural origin and find a wide range of applications such as pharmaceuticals etc [1-3]. It is not surprising therefore that a great protocol of research work is concerned with novel methods for the synthesis of heterocyclic systems [3]. The triazole derivatives are presented in a large number of biologically active molecules. They find use in a wide variety of applications as antibacterial, neuroleptic, hypotensive and spasmolytic agents, most notably as antifungals. On their basis, many pharmaceutical preparations have been created and successfully used such as fluconazole and itraconazole.  In view of the importance of highly functionalized oxindole containing structures, their efficient controlled synthesis remains an important objective.  As a part of a model study for synthesis of highly functionalized oxindole the (3E)-3-[2-(2,4-dichlorophenyl)-2-oxoethylidene]-1,3-dihydro-2H-indol-2-one [4] was exposed to an excess of quaternary aminotriazolium salt in presence of NaOH [5]. Crude reaction products were purified by flash column chromatography on SiO2 (eluent: petroleum ether- ethyl acetate 10-20 %) to give solid compound. The orange solution in MeOH was transferred to a warm beaker and left overnight for crystallization. The next two days, single crystals were separated from the solution. In the IR spectrum the peaks at 3506 and 3301 cm–1 were diagnostic of the primary amine group. In the 1H NMR spectrum, the NH protons were observed at δ = 10.56 and 9.1 ppm, NH2 protons were observed at δ = 10.56 and 10.08 ppm as two singlets. In the 13C NMR spectrum, triazol‘s carbons resonated at δ = 159.9 ppm, the carbon attached to amino group resonated at δ = 147.9 ppm. Further the stereochemistry of (3Z)-3-{(2Z)-1-amino-2-(2,4-dichlorophenyl)-2-[(4H-1,2,4-triazol-4-yl)imino]ethylidene}-1,3-dihydro-2H-indol-2-one was confirmed as Z selectivity based on its single crystal X-ray diffraction analysis.Compound crystallizes in the monoclinic P21/n space group,  a = 8.2232(3), b = 29.8877(10), c = 14.4864(6) Å,  ß = 94.507(3)°, V = 3549.4(2) Å3, Z=8, Z‘=2. The symmetry independent molecules have the same configuration in respect of double C=C and C=N bonds, but differ by orientation of benzene and triazole rings.