14135-63-8

Usage

Synthesis Reference(s)

Synthetic Communications, 21, p. 1021, 1991 DOI: 10.1080/00397919108019791

InChI:InChI=1/C10H8N2O/c13-10-7-4-8-11-12(10)9-5-2-1-3-6-9/h1-8H

Upstream product

• 130472-36-5 N'-[(E)-3-Ethoxycarbonyl-prop-2-en-(Z)-ylidene]-N,N,N-trimethyl-hydrazinium; iodide 
• 100-63-0 phenylhydrazine 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 20672-18-8 2-(phenylhydrazono)ethanal 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 83297-09-0 5-(1,2-diaza-1-phenylbutadien-4-ylidene)-2,2-dimethyl-1,3-dioxan-4,6-dione 
• 504-30-3 2H-Pyridazin-3-one 
• 591-50-4 iodobenzene 
• 1698-54-0 6-hydroxy-2-phenyl-3(2H)-pyridazinone 
• 166328-14-9 potassium (furan-2-yl)trifluoroboranuide 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 1698-57-3 6-chloro-2-phenylpyridazine-3(2H)-one 

Downstream Products

• 143998-65-6 2-Phenyl-5-(toluene-4-sulfonylmethyl)-2H-pyridazin-3-one 
• 143998-63-4 2-Phenyl-4-(toluene-4-sulfonylmethyl)-2H-pyridazin-3-one 
• 143998-67-8 3-Phenyl-7-(toluene-4-sulfonyl)-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one 

Relevant academic research and scientific papers

A new mild synthetic route to N-arylated pyridazinones from aryldiazonium salts

An efficient method for the synthesis of N-arylated pyridazinones from potassium 2-furantrifluoroborate and aryldiazonium salts is described. The reaction was run in water at 0-5 °C in short reaction times and without any catalyst or additive. A mechanistic proposal is made based on the experimental data and DFT calculations. the Partner Organisations 2014.

Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides

Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions (50-82°C). The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al (1c) generates a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of diethyl malonate, ethyl cyanoacetate, and malononitrile with aryl iodides under mild conditions (50-82°C). The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles.

A new and convenient synthesis of 3(2H)-pyridazinones by reacting carbanion of ethyl trimethylsilylacetate with phenylhydrazones

A one-pot synthesis of 5,6-disubstituted-2-phenyl-3(2H)-pyridazinones 4 is achieved on treatment of carbanion of ethyl trimethylsilylacetate with phenylhydrazones of 1,2-dicarbonyl compounds 1.

Reaction of triethyl phosphonoacetate anion with phenylhydrazones: A new method for the preparation of 3(2H)-pyridazinones

Various 5,6-disubstituted-2-phenyl-3(2H)-pyridazinones 4 have been synthesised by reacting triethyl phosphonoacetate anion with monophenylhydrazone of 1,2-dicarbonyl compounds 2.

(E)-Ethyl β-formylacrylate Dimethylhydrazone Methiodide: a Reactive and Convenient Precursor of (E)-Ethyl-β-formylacrylate

The methiodide of (E)-Ethyl-β-formylacrylate dimethylhydrazone is readily prepared in two steps.It gives rise to regioselective 1,4-additions and is a stable and convenient precursor of (E)-Ethyl-β-formylacrylate.

The Reaction of Meldrum's Acid with α-Dicarbonyl Monohydrazones: A New Synthesis of Pyridazin-3-ones

Treatment of the monohydrazones of α-dicarbonyl compounds with Meldrum's acid gives the condensation products (13)-(19) under standard conditions.Reaction of pyruvaldehyde 2-phenylhydrazone or 2-t-butylhydrazone with Meldrum's acid at 80 deg C gives the corresponding 2-substituted-2,3-dihydro-6-methyl-3-oxo-pyridazine-4-carboxylic acids (29) and (30).Cyclisation of the other N-monosubstituted condensation products (13), (14), (16), (18), and (19) to 3-oxopyridazine-4-carboxylic acids (31)-(35) can be effected under basic conditions.Gas-phase pyrolysis of the N-aryl derivatives (13)-(16) at 550 deg C and 10E-2 Torr gives N-arylpyridazin-3-ones (38)-(41) while the N-t-butyl derivatives (18) and (19) at 750 deg C and 10E-2 Torr give N-unsubstituted pyridazin-3-ones (44) and (45) by additional loss of 2-methylpropene. 2-t-Butylpyridazin-3-ones (42) and (43) can be isolated from the same precursors under milder conditions (500 deg C and 10E-2 Torr).Pyrolysis of the N,N-dimethyl derivative (17) gave only polymeric material.