3815-83-6

Usage

InChI:InChI=1/C14H10N2O2/c17-14-13(11-7-3-1-4-8-11)16(15-18-14)12-9-5-2-6-10-12/h1-10H

Upstream product

• 591-50-4 iodobenzene 
• 508191-77-3 3-phenylsydnone 
• 7664-93-9 sulfuric acid 
• 3684-12-6 2-phenyl-2-(phenylamino)acetic acid 
• 67-64-1 acetone 
• 122665-69-4 4-copper-3-phenylsydnone 
• 13183-09-0 3-phenyl-4-bromosydnone 
• 103-01-5 N-Phenylglycine 
• 6415-68-5 N-nitroso-N-phenylglycine 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 52827-05-1 DL-2-(N-Nitrosoanilino)-2-phenylessigsaeure 

Downstream Products

• 20375-28-4 N-Phenyl-ethylbenzhydrazonat 
• 231289-36-4 C,N-Diphenylnitrilimine 
• 1002334-26-0 1,3,5-triphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 1002334-27-1 1,5-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)-1H-pyrazole 
• 70784-90-6 4-(1,5-diphenyl-1H-pyrazol-3-yl)-N,N-dimethylaniline 
• 17355-75-8 ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate 
• 53561-07-2 1,5-diphenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 67491-64-9 dimethyl 1,5-diphenyl-1H-pyrazole-3,4-dicarboxylate 
• 62248-95-7 1-aza-cyclohepta-1,2,4,6-tetraene 
• 124-38-9 carbon dioxide 
• 622-16-2 diphenylcarbodiimide 
• 100-47-0 benzonitrile 
• 41555-25-3 dimethyl 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylate 
• 71331-54-9 5-oxo-3,4-diphenyl-2,5-dihydro-[1,2,3]thiadiazolium betaine 

Relevant academic research and scientific papers

Sydnone Reporters for Highly Fluorogenic Copper-Free Click Ligations

Bioorthogonal fluorescent turn-on reactions are attractive for the sensitive real-time detection of a variety of phenomena including bioconjugation, chemical reactivity, and material assembly. Herein we describe the use of 3,4-disubstituted sydnones, a singular class of mesoionic dipoles, for highly fluorescent turn-on copper-free click cycloadditions with the fluorogenic dibenzocyclooctyne Fl-DIBO. Coherent with time-dependent density functional theory calculations, the pyrazole cycloadducts were found to be highly fluorescent with compelling photophysical properties including excellent fluorescence enhancement (up to 240-fold), high quantum yields (over 45%), and large Stokes shift (over 100 nm). Furthermore, the good stability and reactivity of 4-chlorosydnones with Fl-DIBO allowed us to employ them as chemical reporters for the challenging detection of modified-proteins in complex cellular extracts, with exquisite specificity in no-wash conditions. This novel fluorogenic system significantly expands our chemical biology toolbox and should be beneficial in countless applications.

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

An easy direct arylation of 3-arylsydnones

An easy one-step synthesis of 3,4-diarylsydnones from 3-arylsydnones and arylboronic acids by Pd-catalyzed C-H bond activation is described. Georg Thieme Verlag Stuttgart New York.

Palladium-catalysed direct arylation of sydnones

Conditions for the palladium-catalysed direct arylation of sydnones with aryl iodides and bromides are revealed. Georg Thieme Verlag Stuttgart.

Cross coupling of bromo sydnones: Development of a flexible route toward functionalized pyrazoles

(Chemical Equation Presented) The application of a Suzuki cross coupling approach to a range of C-4 substituted sydnones from a 4-bromosydnone is described. Moreover, the potential of this approach to prepare a diverse range of pyrazoles is demonstrated.

Synthesis of aryl- and vinyl-sydnones. Cross-coupling of 4-copper-3-phenylsydnone with aryl and vinyl halides catalyzed by palladium(0) complexes

A general method is suggested for introduction of substituents into the 4-position of 3-phenylsydnone by palladium(0) catalyzes cross-coupling of 4-copper-3phenyl-sydnone with aryl iodides and vinyl bromides.

Pyrrolo-1,3,4-thiadiazole Derivatives from Mesomeric Heteropentalenes and Azodicarboxylic Esters

The mesomeric heteropentalene betaines of type 4,7, and 18 display an unusual reaction behavior against the azodicarboxylic esters 8a-c.Surprisingly, 4 reacts with 8a,b to produce 17a,b, whereas the reaction of 4 with 8c leads to 11 and the novel azomethine imine 15.Also the reaction of 18 with 8a-c gives in two cases 20 or 25 beside the azomethine imine 19.Furthermore, 7 reacts with 8a to form 26, whereas the reaction of 7 with 8c surprisingly yields 29.Spectroscopic data as well as the results of the X-ray analyses of 17a and 19 are consistent with the structures.