Synthesis and structure of new 1,3,5-triazine-pyrazole derivatives

Mikhaylichenko, Svetlana; Patel, Saurabh M.; Dalili, Shadi; Chesnyuk, A. A.; Zaplishny, V. N.

doi:10.1016/j.tetlet.2009.03.054

Cited by 34 publications

(25 citation statements)

References 11 publications

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“…For background to chalcone synthesis and the biological activity of pyrazole derivatives, see: Bekhit et al (2008); Ono et al (2007); Cottineau et al (2002); Gadakh et al (2010); Hall et al (2008); Hoepping et al (2007); Mikhaylichenko et al (2009); Park et al (2005) Souza et al (2002); Xie et al (2008). For related structures, see; Chantrapromma et al (2009); Suwunwong et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

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3-(4-Bromophenyl)-5-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide

2011

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The molecule of the title pyrazole derivative, C18H19BrN4S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromophenyl ring, whereas it is inclined to the 4-(dimethylamino)phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethylamino group is slightly twisted from the attached benzene ring [C—C—N—C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, molecules are linked by intermolecular N—H⋯S hydrogen bonds into chains along [20]. The crystal is further stabilized by C—H⋯π interactions.

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Section: Related Literaturementioning

confidence: 99%

“…The pyrazole moiety is one of the core structures in a number of natural products (Xie et al, 2008). Numerous compounds which contain the pyrazole moiety are known to exhibit a wide range of biological properties such as antihypertensive (Mikhaylichenko et al, 2009), analgesic (Hall et al, 2008), anti-inflammatory (Bekhit et al, 2008),…”

Section: Data Collectionmentioning

confidence: 99%

3-(4-Bromophenyl)-5-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide

2011

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“…The 2,4,6-trichloro-1,3,5-triazine (TCT), so-called cyanuric chloride, is an important triazine derivative and a well-known precursor in organic synthesis. [1][2][3][4][5][6][7][8][9][10][11] This precursor have become a very attractive field of research by virtue of the applications that can be envisaged with the obtained products, such as polymers, [12][13][14][15] non-linear optical materials [16][17][18] and new photoactive materials. [19][20][21][22][23] A particular interest has been reported on the use of cyanuric chloride in reactive dyes 24 since they are able to bond hydroxy groups from the cellulose and amino or thiol from proteins or polyamides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and photophysical properties of ESIPT reactive triazine derivatives

Kuplich¹,

Grasel²,

Campo³

et al. 2012

J. Braz. Chem. Soc.

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Uma série de quatro compostos fotoativos derivados da triazina foi obtida a partir da substituição nucleofílica aromática no cloreto cianúrico. Os compostos foram caracterizados por espectroscopia de infravermelho (IR) e ressonância magnética nuclear (NMR de 1 H e 13 C), além de espectrometria de massas de alta resolução (HRMS MALDI). A espectroscopia de absorção na região do UV-Vis e a emissão de fluorescência (no estado sólido e em solução) foram também utilizadas para estudar o comportamento fotofísico destes compostos. Os derivados obtidos são fluorescentes na região do azul-laranja por um mecanismo de transferência protônica intramolecular no estado excitado e apresentam um grande deslocamento de Stokes (6365-10290 cm-1). Os derivados sintetizados neste trabalho reagiram com sucesso com fibras de celulose para dar novos compostos celulósicos fluorescentes. Four new reactive fluorescent triazine derivatives were obtained from nucleophilic aromatic substitution of cyanuric chloride. The compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance (13 C and 1 H NMR) and high resolution mass spectrometry (HRMS MALDI). UV-Vis and steady-state fluorescence (in solution and in solid state) spectroscopies were also applied to characterize the photophysical behavior. The dyes are fluorescent by an intramolecular proton transfer mechanism (ESIPT) in the blue-orange region, with a large Stokes shift between 6365-10290 cm-1. The fluorescent cyanuric derivatives could successfully react with cellulose fibers to give new fluorescent cellulosic materials.

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“…However, the reaction of 1,1,1-trifluoropentane-2,4dione with 4,6-disubstituted 2-hydrazinyl-1,3,5-tetrazines resulted in the corresponding heterocycles 91b. 151 Since a-fluoro-substituted b-diketones exist in the ketone form, nucleophilic attack of the terminal amino group of phenylhydrazine occurs on the more electrophilic carbonyl group C(O)CF 3 to form regioisomer 91a. 68,152 Reaction of 2-trifluoromethyl-substituted cyclic 1,3diketones 22 (n = 1, 2) with hydrazine, methyl-and phenylhydrazines occurs regiospecifically to form 3-trifluoromethylpyrazoles 93a.…”

Section: Reaction With Nn-and No-dinucleophilesmentioning

confidence: 99%