94377-89-6

Upstream product

• 108-94-1 cyclohexanone 
• 98-88-4 benzoyl chloride 
• 17040-65-2 1-cyclohexenyl(phenyl)methanone 
• 100-63-0 phenylhydrazine 
• 1001386-09-9 (2-bromocyclohex-1-en-1-yl)(phenyl)methanone 
• 591-50-4 iodobenzene 
• 14714-06-8 1-phenyl-4,5,6,7-tetrahydro-1H-indazole 
• 16492-56-1 1,3-diphenyl-3a,4,5,6,7,7a-hexahydro-1H-indazole 
• 3580-38-9 2-Benzoylcyclohexanone 
• 100-52-7 benzaldehyde 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 588-64-7 benzaldehyde phenylhydrazone 
• 39207-77-7 2-methylenecyclohexan-1-yl phenyl ketone 
• 918497-00-4 α-chlorobenzaldehyde phenylhydrazone 

Relevant academic research and scientific papers

Palladium-catalyzed cyclization of β-bromo-α,β-unsaturated ketones with arylhydrazines leading to 3-substituted 1-aryl-1 H-pyrazoles

β-Bromo-α,β-unsaturated ketones are condensed with arylhydrazines to form hydrazones, which are in situ intramolecularly cyclized into 3-substituted 1-aryl-1 H-pyrazoles under a catalytic system of Pd(OAc) 2/1,3-bis(diphenylhosphino)propane (dppp)/NaOtBu. Copyright

The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles

In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.

Corrigendum to “AlCl3-promoted reaction of cycloalkanones with hydrazones: A convenient direct synthesis of 4,5,6,7-tetrahydro-1H-indazoles and their analogues” (Tetrahedron Letters (2019) 60(35), (S0040403919307439), (10.1016/j.tetlet.2019.150988))

The authors regret that the printed version of the above article contained errors in Tables 1 and 2. A plausible mechanism was proposed using 1-benzylidene-2-phenylhydrazine 1a and cyclohexanone 2a as model reactants (Scheme 2). The formation of aluminum

AlCl3-promoted reaction of cycloalkanones with hydrazones: a convenient direct synthesis of 4,5,6,7-tetrahydro-1H-indazoles and their analogues

The AlCl3-promoted reactions of cycloalkanones with hydrazones are described. This approach represents a mild and operationally simple method to access 2,3-diaryl-4,5,6,7-tetrahydro-1H-indazoles and their analogues in good to moderate yields.

Csp3Csp3 bond cleavage in the palladium-catalyzed aminohydroxylation of allylic hydrazones using atmospheric oxygen as the sole oxidant

A C-C bond cleavage was observed in the palladium-catalyzed aminohydroxylation of allylic hydrazones, using atmospheric oxygen as the sole oxidant. This reaction could also proceed in a one-pot manner, starting from keto-alkene compounds and phenylhydrazine.

A robust protocol for Pd(ii)-catalyzed C-3 arylation of (1H) indazoles and pyrazoles: Total synthesis of nigellidine hydrobromide

C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmaceuticals. C-3 C-H arylation of (1H) indazole and pyrazole has been a significant challenge due to the poor reactivity of the C-3 position. Herein, we report a practical Pd(ii)/Phen catalyst and conditions for the direct C-3 arylation of indazole and pyrazole with ArI or ArBr without using Ag additives as halide scavengers. The use of toluene, chlorobenzene, trifluoromethylbenzene and mesitylene as the solvent was found to be crucial for the selectivity and reactivity. We further demonstrate the robustness of this protocol through the first total synthesis of nigellidine hydrobromide as well as the expedient preparation of heterocycles structurally related to pesticides and drug molecules.

Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives

The reaction of hydrazine derivatives with α,β-unsaturated ketones, such as cyclohexenyl(phenyl)methanone and (E)-2-benzylidenecyclohexanone, were investigated. The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product.

1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2

Novel 1,3-diarylcycloalkanopyrazoles 1, and diphenyl hydrazides 2 were identified as selective inhibitors of cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.