5591-70-8

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 7, p. 259, 1964 DOI: 10.1021/jm00333a004

Upstream product

• 57488-21-8 (Z)-2-phenyl-3-(piperidin-1-yl)acrylonitrile 
• 613-90-1 benzoyl cyanide 
• 140-29-4 phenylacetonitrile 
• 70515-61-6 (E)-3-(dimethylamino)-2-phenylacrylonitrile 
• 140-69-2 4-methoxybenzylhydrazine 
• 1823-91-2 1-phenylethyl cyanide 
• 70205-70-8 2-dimethylaminomethylene-2-phenylacetonitrile 
• 5841-70-3 phenyl(formyl)acetonitrile 
• 31881-80-8 (Z)-2-phenyl-3-(p-tolylamino)acrylonitrile 
• 18226-53-4 2-phenyl-3-(piperidin-1-yl)acrylonitrile 

Downstream Products

• 32016-25-4 7-amino-3,6-diphenylpyrazolo<1,5-a>pyrimidine 
• 129095-38-1 6-cyclohexyl-6,7-dihydro-3-phenyl-4H-pyrazolo<1,5-a>pyrrolo<3,4-d>pyrimidine-5,8-dione 
• 117411-51-5 N-carbethoxy-N¹-(4-phenyl)pyrazol-3-yl-thiourea 
• 130506-84-2 6-acetyl-7-methyl-3-phenylpyrazolo<1,5-a>pyrimidine 
• 12108-09-7 3-azo-4-phenylpyrazole 
• 73997-07-6 3,8-Diphenyl-pyrazolo<5,1-d>-1,2,3,5-tetrazin-4(3H)-on 
• 109013-07-2 3-Methyl-8-phenyl-pyrazolo<5,1-d>-1,2,3,5-tetrazin-4(3H)-on 
• 109013-06-1 3-(4-Nitrophenyl)-8-phenyl-pyrazolo<5,1-d>-1,2,3,5-tetrazin-4(3H)-on 
• 91120-56-8 7'-Phenylspiropyrazolo<5,1-c><1,2,4>triazol>-10-on 
• 91120-75-1 2,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-on-(4-phenyl-1H-pyrazol-5-yl)hydrazon 
• 91120-57-9 2,3,4,5,7'-Pentaphenylspiro<2,4-cyclopentadien-1,3'-<3H>pyrazolo<5,1-c><1,2,4>triazol> 
• 99898-70-1 8-phenyl-2-thioxo-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one 
• 79441-89-7 4,8-Diphenyl-pyrazolo[5,1-c][1,2,4]triazine 
• 99898-74-5 2-methylthio-4-chloro-8-phenylpyrazolo<1,5-a>-s-triazine 

Relevant academic research and scientific papers

HETEROCYCLE SUBSTITUTED AMINO-PYRIDINE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to heterocycle substituted amino-pyridine compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.

Copper-catalyzed N-aryl-β-enaminonitrile synthesis utilizing isocyanides as the nitrogen source

A novel synthetic protocol for N-aryl-β-enaminonitriles, which are useful building blocks for heterocycle synthesis, was developed using isocyanides as the nitrogen source. Using copper-catalyzed one-step reactions between isocyanides and benzyl cyanides under mild conditions, diverse N-aryl-β-enaminonitriles could be synthesized in excellent yields and with high atom-efficiency. N-Alkyl-β-enaminonitriles were also synthesized in good yields. A mechanism involving an imidoyl-copper intermediate was proposed based on mechanistic studies and previous reports. In addition, we demonstrated that a synthesized N-aryl-β-enaminonitrile could be utilized for the synthesis of a β-keto nitrile compound and 3-aminopyrazole.

Structure and tautomerism of 4-substituted 3(5)-aminopyrazoles in solution and in the solid state: NMR study and Ab initio calculations

Annular tautomerism of 3(5)-aminopyrazoles containing a cyano, thiocyanato, or aryl substituent in the 4-position has been studied by 1H and 13C NMR in solution, cross-polarization and magic-angle spinning 13C NMR in the s

Synthesis and biological evaluation of 7-trifluoromethylpyrazolo[1,5-a]pyrimidines as anti-inflammatory and antimicrobial agents

A series of 2-H/methyl-3-phenyl-5-alkyl/aryl/heteroaryl-7-trifluoromethylpyrazolo[1,5-a]pyrimidines (4a-l) were synthesized by refluxing 3(5)-amino-4-phenyl-5(3)-H/methyl-1H-pyrazoles (1-2) with trifluoromethyl-?2-diketones (3a-f) in ethanol for 6 h. The

β-Amination of saturated nitriles through palladium-catalyzed dehydrogenation, 1,4-addition, and re-dehydrogenation

Amination at the β-position of 2-arylpropionitriles through catalytic dehydrogenation occurred by using [PdCl2(PMe3) 2] catalyst and bromobenzene. This is the first catalytic reaction involving the direct dehydrogenation of saturated nitriles.

Study of regioselectivity of reactions between 3(5)-aminopyrazoles and 2-acetylcycloalkanones

Regioselectivity was examined of reactions between nine 3(5)-aminopyrazoles and 2-acetylcyclopentanone and 2-acetylcyclohexanone under various conditions. A series of cyclopenta[e]pyrazolo-[1,5-a]pyrimidines was obtained. The highest regioselectivity of the reaction was observed in alcohol at 20°C in the presence of a catalytic quantity of trifl uoroacetic acid. The regiostructure of compounds was established by 1H and 13C NMR spectroscopy. Pleiades Publishing, Ltd., 2012.

Synthesis and biological evaluation of novel (4 or 5-aryl)pyrazolyl-indoles as inhibitors of interleukin-2 inducible T-cell kinase (ITK)

Interleukin-2 inducible T-cell kinase (ITK) is one of five kinases that belong to the Tec kinase family that plays an important role in T-cell and mast cell signaling. Various reports point to a role of ITK in the treatment of allergic asthma. For example, it was shown that mice lacking ITK have reduced airway hyperresponsiveness, inflammation and tracheal responses in an allergic asthma model. In this article, we disclose novel ITK inhibitors based on (4 or 5-aryl)pyrazolyl-indole scaffold that were also found to be selective for ITK over other kinases like IRK, CDK2, GSK3ss and PKA.

Studies with enaminonitriles: Synthesis and chemical reactivity of 2-phenyl-3-piperidin-1-yl acrylonitrile under microwave heating

(Chemical Equation Presented) Benzyl cyanide reacts with triethylorthoformate and piperidine in DMF solution to yield the title compound 2. This reacted with aromatic amines to yield either aminoacrylonitriles orquinoline depending on reaction conditions and substitution pattern on the aromatic amine. The reaction of compound 2 with hydrazine hydrate could only be effected in the microwave oven and resulted in the formation of aminopyrazole 7. Diazotization of 7 and coupling with an active methylene reagent afforded pyrazolo[5,1-c]-[1,2,4]triazine derivatives.

2H-Pyrazol-3-ylamines as precursors for the synthesis of polyfunctionally substituted pyrazolo[1,5-a]pyrimidines

Substituted aminopyrazoles (5a-d) were synthesized and reacted with bidentate electrophiles to afford pyrazolo[1,5-a]pyrimidines. The regioorientation of reagents has been determined by (15N, 1H) HMBC measurements as well as an X-ray crystal structure determination. ARKAT.

Pyrazolotriazine compounds

Pyrazolotriazine compounds of the formula: STR1 wherein R1 is OH or alkanoyloxy; R2 is H, OH, or SH; R3 is (1) unsaturated N- or S-containing heterocyclic group optionally having 1-2 substituents of halogen, nitro or phenylthio, (2) naphthyl, (3) phenyl optionally having 1-3 substituents of (i) alkyl, (ii) phenyl, (iii) alkoxycarbonyl, (iv) cyano, (v) nitro, (vi) alkoxy, (vii) phenylalkoxy (viii) phenylthio-alkyl, (ix) phenoxy, (x) STR2 R is alkyl, halo-substituted alkyl, phenyl optionally having 1-3 substituents, or pyridyl, and l is 0, 1 or 2, (xi) halogen, (xii) phenylalkyl, (xiii) carboxy, (xiv) alkanoyl, (xv) benzoyl optionally having 1-3 substituents, (xvi) amino, (xvii) OH, (xviii) alkanoyloxy, (xix) STR3 or (xx) STR4 (A is alkylene), said compounds having a xanthine oxidase inhibitory activity and are useful for the prophylaxis and treatment of gout.