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Upstream product

• 64-17-5 ethanol 
• 3815-83-6 3,4-diphenylsydnone 
• 73876-41-2 C₁₃H₁₀N₂⁽¹⁵⁾N₂ 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 588-64-7 benzaldehyde phenylhydrazone 
• 918497-00-4 α-chlorobenzaldehyde phenylhydrazone 
• 18039-45-7 2,5-diphenyl-2H-tetrazole 

Downstream Products

• 16492-48-1 1,3-Diphenyl-4,7-methano-3a,4,5,6,7,7a-hexahydro-indazol 
• 98055-36-8 1,3,7a-Triphenyl-5,6,7,7a-tetrahydro-pyrrolo<2,1-b>-1,2,4-triazol 
• 104860-96-0 (3aS,4S,9bS)-4-Methyl-1,3-diphenyl-3a,4,5,9b-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline 
• 98055-40-4 1,3-Diphenyl-10b-methyl-5,6,10b,11-tetrahydro-isochinolino<2,1-b>-1,2,4-triazol 
• 104860-98-2 (3aS,4S,9bS)-4-Ethyl-1,3-diphenyl-3a,4,5,9b-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline 
• 7189-13-1 1,3,4,5-tetraphenyl-1H-pyrazole 
• 104861-01-0 (3aS,4S,9bS)-4-Butyl-1,3-diphenyl-3a,4,5,9b-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline 
• 130542-49-3 C₂₉H₂₁N₃O₃S 
• 130542-44-8 C₂₉H₂₂N₂OS 
• 116857-85-3 1,3-diphenyl-4,5-diacetylpyrazole 
• 116857-84-2 1,3-diphenyl-4,5-diacetyl-4,5-dihydropyrazole 
• 7189-05-1 1-(1,3-diphenyl-1H-pyrazol-4-yl)ethan-1-one 
• 126664-53-7 C₂₅H₂₀N₂O₂S 
• 126664-61-7 C₂₅H₂₀N₂O₂S 

Relevant academic research and scientific papers

Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones

The thiocarbonyl group of 4,5-dichloro-1,2-dithiole-3-thione reacts as a 1,3-dipolarophile towards diaryl nitrile imines by 1,3-dipolar cycloaddition followed by opening of the dithiole ring with loss of sulfur to give 5-methylene-1,3,4-thiadiazolines; th

π-face-selective 1,3-dipolar cycloadditions of 3,4-Di-tert- butylthiophene 1-oxide with 1,3-dipoles

3,4-Di-tert-butylthiophene 1-oxide underwent 1,3-dipolar cycloadditions with 1,3-dipoles such as nitrile oxide, diazomethane, nitrile imide, nitrone, and azomethine ylide at its syn-π-face with respect to the S=O bond. Taylor & Francis Group, LLC.

Sydnone photochemistry: Direct observation of earl's bicyclic lactone valence isomers (oxadiazabicyclo[2.1.0] pentanones), formation of carbodiimides, reaction mechanism, and photochromism

The matrix photolyses of 3-phenyl-, 3-pyridyl, and 3,4-diphenylsydnones 16, 19, and 22 were investigated by matrixisolation infrared spectroscopy. The formation of the neutral, bicyclic lactone valence isomers postulated by Earl - the oxadiazabicyclo[2.1.0]pentanones exo-17 and exo-20 - was clearly observed in the first two cases and is also likely in the case of exo-23 (C=Oabsorptions in the IR at 1881, 1886, and 1874 cm -1, respectively). The efficient photodecomposition of sydnones to carbodiimides RN=C=NR0 (18, 21, and 24) and CO2 was established in all three cases. The formation of benzonitrile 27 and azacycloheptatetraene 29 in the matrix photolysis of diphenylsydnone 22 is indicative of diphenylnitrile imine PhCNNPh 26 as an intermediate (2340 cm -11). Neither bicyclic lactones nor carbodiimides have been observed previously in sydnone photochemistry. A general reaction mechanism for the formation of carbodiimides, nitrile imines, and photochromism is put forward. CSIRO 2014.

Nitrile imines: Matrix isolation, IR spectra, structures, and rearrangement to carbodiimides

The structures and reactivities of nitrile imines are subjects of continuing debate. Several nitrile imines were generated photochemically or thermally and investigated by IR spectroscopy in Ar matrices at cryogenic temperatures (Ph-CNN-H 6, Ph-CNN-CH317, Ph-CNN-SiMe323, Ph-CNN-Ph 29, Ph3C-CNN-CPh334, and the boryl-CNN-boryl derivative 39). The effect of substituents on the structures and IR absorptions of nitrile imines was investigated computationally at the B3LYP/6-31G level. IR spectra were analyzed in terms of calculated anharmonic vibrational spectra and were generally in very good agreement with the calculated spectra. Infrared spectra were found to reflect the structures of nitrile imines accurately. Nitrile imines with IR absorptions above 2200 cm -1 have essentially propargylic structures, possessing a CN triple bond (typically PhCNNSiMe323, PhCNNPh 29, and boryl-CNN-boryl 39). Nitrile imines with IR absorptions below ca. 2200 cm-1 are more likely to be allenic (e.g., HCNNH 1, PhCNNH 6, HCNNPh 43, PhCNNCH317, and Ph3C-CNN-CPh334). All nitrile imines isomerize to the corresponding carbodiimides both thermally and photochemically. Monosubstituted carbodiimides isomerize thermally to the corresponding cyanamides (e.g., Ph-N=C=N-H 5 Ph-NH-CN 8), which are therefore the thermal end products for nitrile imines of the types RCNNH and HCNNR. This tautomerization is reversible under flash vacuum thermolysis conditions.

Regioselective 1,3-dipolar cycloaddition of nitrilimines to 2-methyl-2-vinyl oxirane

1,3-Dipolar cycloaddition of in situ generated C,N-diaryl nitrilimines to 2-methyl-2-vinyl oxirane gives rise to the regioselective formation of novel 5-(2-methyloxiranyl)-4,5-dihydropyrazole derivatives in moderate to good yields. The structures and ster

Regioselective synthetic approaches towards 1,2,8,9-tetraazadispiro[4.1.4.2]trideca-2,9-dien-6-ones of potential antimicrobial properties

Reaction of 2,5-bis(arylmethylidene)cyclopentanones 1a-d with nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a,b) in 1:2 molar ratio proceeds in a high regioselective manner affording monocycloadducts 3 and dicycloadducts in the form of two isomers 4, 5. Single crystal X-ray diffraction studies of the isolated crystalline form of 3c support the established structure and indicate that the formed product is 7E, 4S, 5R. Antimicrobial activity screening of the synthesized compounds 3-5, utilizing a variety of Gram-positive (Staphylococcus aureus, Enterococcus fecalis and Streptococcus agalactiae), Gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae and Proteus vulgaris) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both Gram-positive and Gram-negative bacteria especially compounds 3b, 4a (antimicrobial active agents against Gram-positive bacteria) and 3c (antimicrobial active agent against Gram-negative bacteria).

Synthesis and reactions of indane-1,3-dione-2-thiocarboxanilides with hydrazonoyl halides and active chloromethylene compounds

A novel synthesis of thiadiazoline derivatives 12 and 14 via treatment of indane-1,3-dione-2-thiocarboxanilides (5) with hydrazonoyl halides 1 and 2 is reported. Also, active chloromethylene compounds 15 react with 5 to give thiazole derivatives 19.

New routes to fused isoquinolines

Treatment of 6,7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides 10 in the presence of Et3N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13, re

Synthesis of novel spiro tetrahydrothiapyranoisoxazolines and pyrazolines

Cis 2,6-Diphenyltetrahydrothiapyranone (1) was subjected to Wittig reaction to generate exocyclic double bond (2a-c). Cycloaddition of nitrile oxides and nitrile imines to the latter led to a novel spiro tetrahydrothiapyranoisoxazolines (3a-f) and spiro t

Studies on chromone derivatives: regioselective 1,3-dipolar and 1,4-cycloaddition reactions of 3-cyano-4H-1-benzopyran-4-thione

1,3-Dipolar cycloaddition reactions of 3-cyano-4H-1-benzopyran-4-thione 1 with nitrilimines 3, nitrile oxides 7 and aldonitrones 8 yielded regioselective cycloadducts involving the thione function.In the latter two classes, the unstable cycloadducts fragmented to yield 3-cyanochromone 11 and isothiocyanate 12 or thioamide 13, respectively.In contrast, dienamines 14 preferred to react at the carbon-carbon double bond in a 1,4-cycloaddition yielding xanthione (9H-xanthene-9-thione) 16 by elimination of HCN and the amine moiety.Keywords: 1,3-dipolar cycloaddition / 1,4-cycloaddition / 4H-1-benzopyran-4-thione / nitrilimine / nitrile oxide / nitrone