36668-22-1

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 100-63-0 phenylhydrazine 

Downstream Products

• 36756-95-3 N-phenyl-C-(2-thienyl)formohydrazidoyl chloride 
• 116709-41-2 1-(5-Methyl-1-phenyl-3-thiophen-2-yl-1H-pyrazol-4-yl)-ethanone 
• 116709-32-1 1-phenyl-3-thien-2-yl-4,5-dihydro-1H-pyrazole-5-carbonitrile 
• 116709-31-0 2-Phenyl-5-thiophen-2-yl-3,4-dihydro-2H-pyrazole-3-carboxylic acid amide 
• 116709-43-4 ethyl 5-methyl-1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carboxylate 
• 116709-45-6 1,5-diphenyl-3-(2-thienyl)-4-cyanopyrazole 
• 116709-44-5 5-Methyl-1-phenyl-3-thiophen-2-yl-1H-pyrazole-4-carboxylic acid phenylamide 
• 116709-34-3 1-Phenyl-3-thiophen-2-yl-1H-chromeno[4,3-c]pyrazol-4-one 
• 116709-42-3 (1,5-Diphenyl-3-thiophen-2-yl-1H-pyrazol-4-yl)-phenyl-methanone 
• 116709-40-1 1,4-diphenyl-3-(2-thienyl)-5-benzoylpyrazole 
• 116709-35-4 1,4-diphenyl-3-(2-thienyl)-5-benzoyl-2-pyrazoline 
• 116709-36-5 Phenyl-(2-phenyl-5-thiophen-2-yl-4-p-tolyl-3,4-dihydro-2H-pyrazol-3-yl)-methanone 
• 116709-38-7 [4-(4-Chloro-phenyl)-2-phenyl-5-thiophen-2-yl-3,4-dihydro-2H-pyrazol-3-yl]-phenyl-methanone 
• 116709-37-6 [4-(4-Methoxy-phenyl)-2-phenyl-5-thiophen-2-yl-3,4-dihydro-2H-pyrazol-3-yl]-phenyl-methanone 

Relevant academic research and scientific papers

A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles

N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is

Synthesis of 3 H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate

A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.

Regioselective Decarboxylative Cycloaddition Route to Fully Substituted 3-CF3-Pyrazoles from Nitrilimines and Isoxazolidinediones

1,4-Diaryl-5-carboxamido substituted 3-trifluoromethylpyrazoles are obtained with exclusive regioselectivity under transition-metal-free conditions. This decarboxylative [3+2] cycloaddition protocol was enabled by employing trifluoromethyl nitrilimines as 1,3-dipoles, and isoxazolidinediones as CO2-masked alkynyl dipolarophiles. The applicability of this method is further manifested by its compatibility with difluoromethyl, alkyl, aryl, and heteroaryl nitrilimines, as well as the preparation of 4-carboxylic amido analogue of drug Celebrex. (Figure presented.).

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

[3+3]-cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ: Access to tetrahydropyridazines

Donor-acceptor cyclopropanes are reacted under the influence of a Lewis acid with hydrazonyl chlorides to afford tetrahydropyridazines. Formally, this transformation can be regarded as a [3 + 3]-cycloaddition of three-membered rings and nitrile imines generated in situ. This efficient method provides fast access to a variety of structurally diverse pyridazine derivatives. The structure of a typical product was confirmed by X-ray crystallography.