644-21-3

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 585, 1986 DOI: 10.1080/00397918608078777

InChI:InChI=1/C8H12N2/c1-2-10(9)8-6-4-3-5-7-8/h3-7H,2,9H2,1H3

Upstream product

• 74-96-4 ethyl bromide 
• 59105-56-5 phenyl-hydrazine; sodium-compound 
• 612-64-6 N-ethyl-N-nitrosoaniline 
• 557-20-0 diethylzinc 
• 100-34-5 benzene diazonium chloride 
• 100-63-0 phenylhydrazine 
• 27843-96-5 (1E)-1-(2-phenylhydrazin-1-ylidene)propan-2-one 
• 75-03-6 ethyl iodide 
• 106087-09-6 3-amino-1-ethyl-4,5-dihydro-1-phenyl-1H-pyrazolium iodide 
• 2684-02-8 benzenediazonium 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 71-41-0 pentan-1-ol 

Downstream Products

• 712-77-6 (ethyl-phenyl-hydrazono)-acetic acid 
• 13271-91-5 N-ethyl-N-phenyl-N'-trimethylsilanyl-hydrazine 
• 121990-82-7 arabino-[2]hexosulose-bis-(ethyl-phenyl-hydrazone) 
• 131197-07-4 1-ethyl-2-(4-chloro-phenyl)-indole 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 13228-39-2 1-ethyl-2-phenyl-1H-indole 
• 58123-28-7 aceton-(ethyl-phenyl-hydrazone) 
• 95003-18-2 Benzophenon-N-ethyl-N-phenylhydrazon 
• 99380-55-9 (E)-2-Ethyl-3-(N'-ethyl-N'-phenyl-hydrazino)-but-2-enenitrile 

Relevant academic research and scientific papers

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles

Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is

N-Isocyanodialkylamines generated in situ for the Joullié–Ugi reaction with indolenines

N-Isocyanodialkylamines are rare isocyanide surrogates for the Ugi-type reactions. To avoid problems with instability and the obnoxious smell of these reagents, we optimized and employed a convenient protocol for in situ dehydration of N,N-dialkyl-N′-formyl hydrazines to give the respective N-isocyanodialkylamines which were utilized in the reaction with indolenines and acetic acid. The reaction was demonstrated to give modest to excellent yields of products incorporating the N-isocyanodialkylamine but not the carboxylic acid component.

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

Discovery of ectoparasiticidal hydrazonotrifluoromethanesulfonanilides

A series of hydrazonotrifluorosulfonanilide derivatives were synthesized and evaluated for in vitro activity against the ectoparasites Ctenocephalides felis and Rhipicephalus sanguineus. Some compounds with excellent activity against tick were identified.

NOVEL HYDRAZINO-CYCLOBUT-3-ENE-1, 2-DIONE DERIVATIVES AS CXCR2 ANTAGONISTS

The present invention relates to novel hydrazino-cyclobut-3-ene-1,2-dione compounds of Formula (I) as selective CXCR2 antagonists, pharmaceutical compositions containing the novel compounds, as well as methods for treating or preventing chemokine mediated

Design, synthesis, and evaluation of novel 3-amino-4-hydrazine-cyclobut-3-ene-1,2-diones as potent and selective CXCR2 chemokine receptor antagonists

We describe herein a novel series of 3-amino-4-hydrazine-cyclobut-3-ene-1,2-diones as potent and selective inhibitors against the CXCR2 chemokine receptor and IL-8-mediated chemotaxis of a CXCR2-expressing cell line. Furthermore, these alkyl-hydrazine series inhibitors such as 5b demonstrated acceptable metabolic stability when incubated in human and rat microsomes.

MEDICINAL COMPOSITION

The present invention is composed of a pharmaceutical composition for the therapy of nephritis which comprises an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof, as an active ingredient: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5 and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted. The pharmaceutical composition of the invention is useful for the therapy of nephritis.

AMIDE DERIVATIVES AND DRUG COMPOSITIONS

The present invention is composed of an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5, and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy, or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted, and a pharmaceutical composition which comprises it as an active ingredient. The compound of the invention is useful as an inhibitor of TGF-β production or an antagonist of TGF-β.