787-84-8

Usage

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 208, 1943The Journal of Organic Chemistry, 49, p. 4014, 1984 DOI: 10.1021/jo00195a028

InChI:InChI=1/C14H12N2O2/c17-13(11-7-3-1-4-8-11)15-16-14(18)12-9-5-2-6-10-12/h1-10H,(H,15,17)(H,16,18)

Upstream product

• 110-86-1 pyridine 
• 5351-66-6 benzoyl thiosemicarbazide 
• 98-88-4 benzoyl chloride 
• 4291-16-1 thioformic acid N'-benzoyl-hydrazide 
• 75-36-5 acetyl chloride 
• 288-88-0 1,2,4-Triazole 
• 288-94-8 1H-tetrazole 
• 3975-85-7 3,5,5-Trimethylpyrazolin 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 584-13-4 4-amino-1,2,4-triazole 
• 3530-15-2 3,5-dimethyl-4H-1,2,4-triazol-4-amine 
• 932-90-1 syn-benzaldehyde oxime 
• 60-29-7 diethyl ether 
• 618-32-6 Benzoyl bromide 

Downstream Products

• 19617-76-6 tribenzoylhydrazine 
• 19447-53-1 tetrabenzoyl-hydrazine 
• 93-97-0 benzoic acid anhydride 
• 16253-60-4 4-(p-anisyl)-3,5-diphenyl-4H-1,2,4-triazole 
• 4073-72-7 3,4,5-triphenyl-1,2,4-triazole 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 35786-99-3 N,N'-diethyl-N,N'-dibenzoyl-hydrazine 
• 35786-98-2 N,N'-dibenzoyl-N,N'-bis-trideuteriomethyl-hydrazine 
• 16152-06-0 3,5-diphenyl-4-m-tolyl-4H-[1,2,4]triazole 
• 1226-43-3 N'-benzoyl-N,N'-dimethylbenzohydrazide 
• 2039-06-7 3,5-diphenyl-1,2,4-triazole 
• 729-44-2 1,2-bis[chloro(phenyl)methylidene]hydrazone 
• 1456-21-9 diphenyl-[1,3,4]thiadiazole 
• 3049-45-4 4-amino-3,5-diphenyl-4H-1,2,4-triazole 

Relevant academic research and scientific papers

1,2-Dibenzoylhydrazine

In the crystal structure of the title compound, C14H12N2O2, the molecule lies about a twofold axis; two carbonyl groups and the H atoms of the N-N bond are in a trans orientation with respect to each other. In the crystal, each molecule is linked to the other and vice versa by intermolecular N-H···O hydrogen bonds between the amide hydrogen and the O atoms of neighbouring molecules to form two ten-membered rings, each of which has the graph-set motif C4R22(10). This extends as a polymeric chain along the c axis.

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

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

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.

Continuous hydrazide preparation method

The invention relates to a continuous hydrazide preparation method. The preparation method includes: in a micro-channel reactor or a pipeline reactor, subjecting esters, anhydrides or acyl chloride tocontinuous reaction with hydrazine or solution of hydrazine under a solvent-free condition or in a solvent to prepare a hydrazide compound. The preparation method is simple, short in technical process, less in waste gas, wastewater and industrial residues, beneficial to environmental production and suitable for industrial production. The adopted reactor is short in reaction time, high in safety and capable of realizing continuous production. The adopted reactor is high in workshop space utilization rate, and large-scale production can be realized. By adoption of the preparation method, solvent recycling can be realized, and production cost is reduced; in addition, high raw material conversion rate, high quality stability and high purity are realized.

N-Methoxyamide: An Alternative Amidation Reagent in the Rhodium(III)-Catalyzed C-H Activation

In the field of transition-metal-catalyzed C-H activation, N-methoxyamides are widely used as C-H activation substrate. Unexpectedly, in this work N-methoxyamides were found to work as efficient amidation reagents in the rhodium(III)-catalyzed C-H activation with boric acid as a cocatalyst. This reaction features broad substrate scope and good yields.

Synthesis and in vitro urease inhibitory activity of benzohydrazide derivatives, in silico and kinetic studies

Benzohydrazide derivatives 1–43 were synthesized via “one-pot” reaction and structural characterization of these synthetic derivatives was carried out by different spectroscopic techniques such as 1H NMR and EI-MS. The synthetic molecules were evaluated for their in vitro urease inhibitory activity. All synthetic derivatives showed good inhibitory activities in the range of (IC50 = 0.87 ± 0.31–19.0 ± 0.25 μM) as compared to the standard thiourea (IC50 = 21.25 ± 0.15 μM), except seven compounds 17, 18, 23, 24, 29, 30, and 41 which were found to be inactive. The most active compound of the series was compound 36 (IC50 = 0.87 ± 0.31 μM) having two chloro groups at meta positions of ring A and methoxy group at para position of ring B. The structure–activity relationship (SAR) of the active compounds was established on the basis of different substituents and their positions in the molecules. Kinetic studies of the active compounds revealed that compounds can inhibit enzyme via competitive and noncompetitive modes. In silico study was also performed to understand the binding interactions of the molecules (ligand) with the active site of enzyme.

Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process

(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.

One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent

A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.

One-Pot Catalytic Approach for the Selective Aerobic Synthesis of Imines from Alcohols and Amines Using Efficient Arene Diruthenium(II) Catalysts under Mild Conditions

A green and efficient catalytic approach for the selective synthesis of imines in air at room temperature was achieved with the aid of newly synthesised diruthenium(II) complexes [(η6-p-cymene)2Ru2Cl2(μ-L)] containing substituted 1,2-diacylhydrazine ligands. All the new complexes were fully characterised by analytical and spectroscopic techniques. The solid-state structure of a representative complex was solved by single-crystal X-ray diffraction analysis. The diruthenium(II) complexes also enable the selective aerobic oxidation of alcohols to aldehydes. The catalytic reaction operates in the presence of air as a green and cheap oxidant, and releases water as the only by-product. A plausible mechanism is proposed for the imine formation, which is believed to proceed via an aldehyde intermediate.