135526-78-2

Basic information

• Product Name: azinox
• Synonyms: Azinox
• CAS NO: 135526-78-2
• Molecular Formula: C19H24N2O2
• Molecular Weight: 312.40606
• Mol File: 135526-78-2.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 544.1°Cat760mmHg
• Flash Point: 254.6°C
• Appearance: /
• Density: 1.22g/cm³
• CAS DataBase Reference: azinox(CAS DataBase Reference)
• NIST Chemistry Reference: azinox(135526-78-2)
• EPA Substance Registry System: azinox(135526-78-2)

Safety Data

• Hazardous Substances Data: 135526-78-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H24N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h4-6,9,15,17H,1-3,7-8,10-13H2

Upstream product

• 79848-93-4 N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide 
• 79-04-9 chloroacetyl chloride 
• 60567-53-5 1-Cyclohexylcarbonylaminomethyl-2-chloracetyl-1,2,3,4-tetrahydro-isochinolin 
• 93255-08-4 Cyclohexanecarboxylic acid bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl-[(methoxymethyl-carbamoyl)-methyl]-amide 
• 87693-75-2 4-(cyclohexylcarbonyl)-6-hydroxy-1-phenethylpiperazine-2-one 
• 94494-35-6 4-(cyclohexylcarbonyl)-3,4-dihydro-1-(2-phenylethyl)-2(1H)-pyrazinone 
• 152189-66-7 N-(2-phenylethyl)-N-(cyanomethyl)amide of cyclohexylcarbonylglycine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 90142-13-5 N-(2,2-dimethoxyethyl)-N-(2-oxo-2-(2-phenethylamino)-ethyl)cyclohexanecarboxamide 
• 97004-08-5 N-(2,2-diethoxy)ethyl-N-2-phenylethyl 2-N-cyclohexylcarbonylaminoacetamide 
• 406954-89-0 1-[2-(2-bromophenyl)ethyl]-4-(cyclohexylcarbonyl)-1,3,4-trihydropyrazin-2-one 
• 32377-88-1 (cyclohexanecarbonyl-amino)-acetic acid 
• 65185-58-2 2-(2-bromophenyl)ethanamine 

Downstream Products

• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 134924-71-3 2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 134924-68-8 2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 57452-31-0 C₁₉H₂₄N₂O₂ 
• 57452-31-0 C₁₉H₂₄N₂O₂ 
• 55375-91-2 (-)-2-Benzoyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline 
• 1463497-65-5 C₁₉H₂₆N₂O 
• 105279-85-4 2-benzyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 5234-86-6 1,3,4,6,7,11b-hexahydro-2H-pyrazino[2,1-a]isoquinoline 
• 1450736-14-7 C₄₁H₄₇N₅O₆ 
• 1403763-79-0 2-2-(cyclohexylcarbonyl)-3-((4-methylpiperazin-1-yl)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 1403763-80-3 2-(cyclohexylcarbonyl)-3-((4-methylpiperidin-1-yl)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 1403763-81-4 2-(cyclohexylcarbonyl)-3-dipropylaminomethyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 1403763-82-5 2-2-(cyclohexylcarbonyl)-3-((2-hydroxyethylamino)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 

Relevant articles and documents

Efficient multicomponent reaction synthesis of the schistosomiasis drug praziquantel

Shorter than ever: A convergent, efficient, and scalable access based on a key Ugi four-component reaction (4CR) followed by a Pictet-Spengler reaction comprises the shortest known synthesis to the schistosomiasis drug praziquantel (see scheme).

Two approaches for the synthesis of levo-praziquantel

We report herein the development of two pathways for the preparation of levo-praziquantel (R-PZQ), which involves three-/four-step processes of a mechanochemical (asymmetric) aza-Henry/acylation reaction, a hydrogenation reaction, (chiral resolution) and a solvent-free acylation-ring closing reaction. The key intermediate (R)-1-aminomethyl tetrahydroisoquinoline could be obtained either by chiral resolution with a rational reuse of the S-isomer or by mechanochemical enantioselective synthesis that refrained from using a bulky toxic solvent. The efficiency and scalability of both the developed routes were demonstrated and desired target product was obtained in a satisfactory yield with excellent enantiopurity (>99%), offering practical, concise and environmentally friendly alternatives to access R-PZQ.

Aza-Henry Reaction with Nitrones, an Under-Explored Transformation

Nitromethylation of nitrones occurred efficiently in CH3NO2 in the presence of tetramethylammonium fluoride or triazabicyclodecene as promoters. The obtained adducts might be conveniently transformed into vicinal diamines. The process was extended to nitroethane and nitropropane affording mixtures of syn and anti stereoisomers with low diastereoselectivity.

Preparation method of praziquantel

The invention relates to the technical field of medical intermediates, and provides a praziquantel preparation method which comprises the following steps: S1, adding isoquinoline, cyanide, tetrabutylammonium bromide and dichloroethane into a reactor, and dropwise adding benzoyl chloride for reaction to obtain a first-step product; s2, performing catalytic hydrogenation on the first-step product to obtain a second-step product; and S3, adding ethyl acetate into the second-step product, stirring and dissolving, adding sodium bicarbonate, dropwise adding chloroacetyl chloride, stirring and reacting to obtain a praziquantel crude product, and recrystallizing to obtain praziquantel. Through the technical scheme, the problems of long reaction process, high energy consumption and low yield in the prior art are solved.

A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides

A series of pharmaceutically relevant small molecules and biopharmaceuticals bearing aliphatic carboxamides have been successfully labeled with carbon-13. Key to the success of this novel carbon isotope labeling technique is the observation that 13C-labeled NiII-acyl complexes, formed from a 13CO insertion step with NiII-alkyl intermediates, rapidly react in less than one minute with 2,2’-dipyridyl disulfide to quantitatively form the corresponding 2-pyridyl thioesters. Either the use of 13C-SilaCOgen or 13C-COgen allows for the stoichiometric addition of isotopically labeled carbon monoxide. Subsequent one-pot acylation of a series of structurally diverse amines provides the desired 13C-labeled carboxamides in good yields. A single electron transfer pathway is proposed between the NiII-acyl complexes and the disulfide providing a reactive NiIII-acyl sulfide intermediate, which rapidly undergoes reductive elimination to the desired thioester. By further optimization of the reaction parameters, reaction times down to only 11 min were identified, opening up the possibility of exploring this chemistry for carbon-11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of 13C-labeled liraglutide and insulin degludec, representing two antidiabetic drugs.