3463-27-2

Usage

InChI:InChI=1/C10H10N2/c1-12-10(7-8-11-12)9-5-3-2-4-6-9/h2-8H,1H3

Upstream product

• 57623-20-8 3-benzoyloxy-1-phenyl-propenone 
• 60-34-4 methylhydrazine 
• 33603-87-1 β-chlorocinnamaldehyde 
• 14804-59-2 β-bromo-cis-cinnamaldehyde 
• 302-15-8 methylhydrazine sulfuric acid 
• 2458-26-6 3-phenylpyrazole 
• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 60-29-7 diethyl ether 
• 34091-51-5 5-iodo-1-methyl-1H-pyrazole 
• 98-80-6 phenylboronic acid 
• 67775-92-2 (Z)-1,1-dimethyl-2-(3-phenylprop-2-ynylidene)hydrazine 

Downstream Products

• 51772-25-9 1,2-dimethyl-3-phenyl-pyrazolium; iodide 
• 105994-77-2 4-bromo-1-methyl-5-phenyl-1H-pyrazole 
• 105994-55-6 4-bromo-1-methyl-3-phenyl-1H-pyrazole 
• 154927-01-2 1-methyl-5-phenyl-1H-pyrazole-4-carbaldehyde 
• 144088-17-5 trans-dichloro{bis(1-methyl-5-phenylpyrazole)}palladium(II) 
• 105994-78-3 1-Methyl-5-phenyl-1H-pyrazole-4-carbonyl chloride 
• 105994-75-0 1-methyl-5-phenyl-1H-pyrazole-4-carboxylic acid 
• 80326-71-2 methyl 1-methyl-5-phenyl-1H-pyrazole-4-carboxylate 
• 198839-96-2 4-deuterio-1-methyl-5-phenylpyrazole 
• 90814-65-6 (E)-3-(N-methylamino)-3-phenylpropenenitrile 
• 3475-07-8 N-methyl-2-phenyl-1H-imidazole 
• 2154-38-3 1-methyl-5-phenyl-1H-imidazole 
• 2411-77-0 N-methyl-4-phenylimidazole 

Relevant academic research and scientific papers

ETHINYL-PYRAZOLE DERIVATIVE

Provided is a novel compound represented by formula [I] or a pharmaceutically acceptable salt thereof having antagonistic activity against group II metabolism-type glutamic acid (m-Glu) receptors. The compound or pharmaceutically acceptable salt thereof i

Synthesis of ynone trifluoroborates toward functionalized pyrazoles

The synthesis of a range of novel ynone trifluoroborates has been achieved, in a two-pot process from propargylic alcohols. These alkynes have been subsequently used in the formation of a range of pyrazole trifluoroborate salts via cyclization with hydrazines. The products are generated with high levels of regiocontrol and in excellent yields and represent versatile synthetic intermediates.

Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage

Propynal hydrazones are successfully converted to the corresponding 3-aminoacrylonitriles in the presence of copper catalysts in good to high yields. As an example, (Z)-N-(hex-2-ynylidene)morpholin-4-amine reacted in the presence of 10 mol % Cu(OAc)2 in acetonitrile at 25 °C to afford (E)-3-morpholinohex-2-enenitrile ((E)-2 h) in 77% yield via C-N bond formation and subsequent β-elimination involving cleavage of N-N and C-H bonds.

Indium-mediated synthesis of heterobiaryls

The palladium-mediated coupling reaction between triorganoindium reagents and organic electrophiles is extended to the synthesis of heteroaromatic compounds. Both electron-rich and electron-poor heterocycles can act as the organic electrophile or as the organoindium derivative.

IMIDAZOPYRIDAZINE COMPOUNDS

The present invention relates to novel substituted imidazo[1,2-b]pyridazine compounds of Formula (I): pharmaceutical compositions thereof, and the use such compounds as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric disorders and neurological diseases.

Photochemistry of Phenyl-Substituted 1-Methylpyrazoles

Direct irradiation of 1-methyl-4-phenylpyrazole (2) in methanol results in regiospecific phototransposition to 1-methyl-4-phenylimidazole (4) and in photocleavage to (E)/(Z)-3-(N-methylamino)-2-phenylpropenenitrile (5) and (E)/(Z)-2-(N-methylaimno)-1-phenylethenyl isocyanide (6). Deuterium labeling confirms that the phototransposition occurs via the P4 permutation pathway. Separate experiments show that 5 and 6 undergo (Z) → (E) isomerization and photocyclization to imidazole 4. Quantum yields for these reactions show that the sequence 2 → 6 → 4 is a major pathway for the P4 phototransposition of 2 → 4. Isocyanides were also detected as intermediates in the P4 phototransposition of a variety of other pyrazoles confirming the generality of this pathway in pyrazole photochemistry. Direct irradiation of 1-methyl-5-phenylpyrazole (3) resulted in the formation of 1-methyl-5-phenylimidazole (7), 1-methyl-2-phenylimidazole (8), and 1-methyl-4-phenylimidazole (4). Deuterium labeling revealed that these products were formed by P4, P6, and P7 permutation pathways, respectively. (E)/(Z)-3-(N-methylamino)-3-phenylpropenenitrile (9) and (E)/(Z)-2-(N-methylamino)-2-phenylethenyl isocyanide (10) photocleavage products were also formed in this reaction. Irradiation of 3 in furan solvent did not result in phototransposition but led to the formation of endo and exo adducts formed by Diels-Alder reaction of furan with 4-phenyl-5-methyl-1,5-diazabicyclo[2.1.0]pent-2-ene. This constitutes the first direct evidence for the formation of a 1,5-diazabicyclo[2.1.0]hex-2-ene from photolysis of a pyrazole and is consistent with the electrocyclic ring closure - heteroatom migration mechanism suggested for the P6 and P7 phototranspositions.

Catalysis and regioselectivity in the Michael addition of azoles. Kinetic vs. thermodynamic control

Bicyclic guanidine bases, TBD and MTBD were found to be high]y efficient catalysts in the Michael addition of azoles with α,β-unsaturated nitriles and esters. The factors influencing regioselectivity have been elucidated, and some new azole-Michael adduct

Thermolyses of 1,1-dimethyl-2-pyrazolinium fluoborates - Evidence for spiro--1-aza-1,4,6-octatrienyl cation

Thermolyses of 3-aryl-1,1-dimethyl-2-pyrazolinium fluoborates give an isomeric mixture of 3-aryl-1-methylpyrazole and 5-aryl-1-methylpyrazole as major products in complete contrast to the corresponding acyclic analogs. 2,6-Diaryl-3-methylpyridines were isolated only in trace quantities.The probable reasons for this unique behaviour was explored using semi-empirical calculations, non-kinetic methods and radiolabelling experiments.A pathway was proposed.

Photochemical Reinvestigation of a 5-Phenyl-2-pyrazoline and Its Product Azocyclopropanes

Irradiation of 1-methyl-5-phenyl-2-pyrazoline (1) affords the previously reported azocyclopropanes 2t and 3t; however, the major product of this reaction is β-(methylamino)-β-phenylpropionitrile (4).Although the azo linkage in 2t and 3t has the trans configuration, irradiation of either isomer causes azo trans -> cis isomerization, slower interconversion of the ring isomers, reversion to pyrazoline 1, and cleavage to styrene.Thermolysis of 2t proceeds twice as fast as that of 3t to interconvert the ring isomers and ultimately to afford exclusively 1.The rapid thermolysis rate of 2t and 3t relative to a model phenylvinylcyclopropane is interpreted in terms of an unusually high facile formation of the α-azo (hydrazonyl) radical.