114382-92-2

Upstream product

• 5874-09-9 methyl (4-methoxyphenyl)carbodithioate 
• 1432595-96-4 (1-hydroxy-3,4-dihydronaphthalen-2-yl)(4-methoxyphenyl)-methanethione 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 100-63-0 phenylhydrazine 
• 49545-59-7 3,3a,4,5-tetrahydro-2,3-diphenyl-2H-benzo[g]indazole 
• 100-52-7 benzaldehyde 
• 6261-32-1 2-benzylidene-1-tetralone 

Relevant academic research and scientific papers

Cyclocondensation of arylhydrazines with 1,3-bis(het)arylmonothio-1,3- diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity

Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2- propenones (prepared in situ by base-induced alkylation of 1,3- monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.

Aromatization and halogenation of 3,3a,4,5-tetrahydro-3-aryl-2-phenyl-2H- benzo[g]indazole using I2/DMSO, CuCl2/DMSO, and N-bromosuccinimide

The treatment of 3,3a,4,5-tetrahydro-3-aryl-2-phenyl-2H-benzo[g]indazoles 4 with I2/DMSO led to the oxidation of the five-member rings (5) as well as the iodination of N-phenyl moieties along with oxidation of the five-member rings (6). However

Isomerization of Substituted Tricyclic 4,5-Dihydropyrazoles

The acid and base catalyzed isomerization of some tricyclic 2-pyrazolines with N-Carbamoyl-, N-thiocarbamoyl- and N-phenyl substituents was investigated. Starting from cis or trans 3-H, 3a-H diastereomers, equilibrium mixtures of cis and trans diastereomers were prepared which were separated and subsequently studied by 1H NMR and 13C NMR spectroscopy. A mechanism for the isomerization of the pyrazolines is suggested, supported by a deuterium exchange at C-3a.