15971-63-8

Upstream product

• 15988-11-1 4-Phenylurazole 
• 542-92-7 cyclopenta-1,3-diene 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 67818-00-2 (Z)-2-(3,5-Dioxo-4-phenyl-[1,2,4]triazolidin-1-yl)-3-hydroxy-but-2-enoic acid ethyl ester 
• 98186-09-5 2-(4-Phenylurazolyl)cyclohexanone 
• 107798-93-6 1-Benzyl-4-phenylurazole 
• 83953-54-2 2-azanorbornadiene 
• 34822-90-7 cyclopentadienylthallium 
• 5164-35-2 bicyclo[2.1.0]pent-2-ene 

Downstream Products

• 195197-65-0 (1R,7S,8R,9S)-8,9-Dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.1.0^2,6]decane-3,5-dione 

Relevant academic research and scientific papers

Copper(II)-catalyzed aerobic oxidation of hydrazides to Azo intermediates and their Diels-Alder versus ene trapping

The oxidation of diethyl 1, 2-hydrazinedicarboxylate using a catalytic Cu(II)-oxazoline system occurs at RT in air, resulting in azo generation, which can then be trapped in situ via hetero-Diels-Alder (HDA) and competitive ene-reactions, with chemoselect

Reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione and Diethylazocarboxylate in [4+2]-Cycloaddition and Ene Reactions: Solvent, Temperature, and High-Pressure Influence on the Reaction Rate

We have studied the solvent, temperature, and pressure influences on the reaction rates of cyclic and acyclic N=N bonds in the Diels-Alder and ene reactions. The transfer from N-phenylmaleimide (9) to a structural analogue, 4-phenyl-1,2,4-triazoline-3,5-dione (2), is accompanied by the rate increase in five to six orders of magnitude in the Diels-Alder reactions with cyclopentadiene (4) and 9,10-dimethylanthracene (5), whereas the transfer from dimethyl fumarate (10) to diethyl azodicarboxylate (1) increases only in one to two orders of magnitude. The ratio of the reaction rate constants (2 + 4)/(1 + 4) is very large (5.2 × 107) and almost the same (5.3 × 107) as in the ene reactions with tetramethylethylene (7), (2 + 7)/(1 + 7). It has been observed that the N=N bond in reagent 2 has strong electrophilic, and its N-N moiety in the transition state has nucleophilic properties, which results from the analysis of the solvation enthalpy transfer of reagents, activated complex, and adduct in the Diels-Alder reaction of 2 with anthracene 22.

Electrosynthesis of cyclic α-carbonylazo compounds. Chemical stability of the electrogenerated dienophiles and in situ trapping of dienes

Dienophilic cyclic α-carbonylazo compounds were prepared electrochemically by oxidation of the corresponding hydrazino compounds using a flow cell fitted with a graphite felt anode in acidic methanol or acetonitrile. The instability of these compounds in methanol was first studied. In situ Diels-Alder additions of these electrogenerated dienophiles and various dienes were performed in relatively good yields in acidic methanol or acetonitrile.

Anodic co-oxidation of urazole and ferrocenes: First trapping of cyclopentadienols

Cyclopentadien-5-ols, the major products resulting from decomposition of some ferrocenium cations by molecular oxygen, are regio- and stereo-selectively trapped by 4-phenyl-1,2,4-triazoline-3,5-dione.

Biocatalysis in the chiral recognition of meso-diamides - An efficient route from cyclic olefinic hydrocarbons to optically pure diamino-polyols

meso-Diamino-di(tri,tetr)ols 1-8 were synthesized starting from cheap carbocyclic olefins and cis-diepoxy derivatives. Enantioselective hydrolysis of the corresponding bis(phenylacet)amides with penicillin amidase from E. coli (EC 3.5.1.11) was effected in good yields (73-90%) and with high optical purities (ee 91 - >97).

Stereospecific vs stereoselective bromination of non-conjugated heterocyclic alkenes

4-Substituted triazolinediones have been reacted with cyclopentadiene monomer, and the resultant cycloadducts (1a,b) treated with bromine in carbon tetrachloride.Contrary to expectation, addition of bromine to carbon-carbon double bond occurs via syn-addition in a stereospecific manner.The above triazolinediones have also been reacted with 1,3-cyclohexadiene and the resultant adducts (2a,b) subjected to bromination in carbon tetrachloride.In this case two products (trans and cis) are formed in a stereoselective manner.

5-Fluorocyclopentadiene: Synthesis and Utility

5-Fluorocyclopentadiene 2 has been prepared by the reaction of cyclopentadienylthallium and the F(+) source, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclooctane bis(tetrafluoroborate).In their reactions with compound 2, dienophiles form adducts having exclusively syn orientation.

2-azanorbornadiene

The unstable and hitherto unknown 2-azanorbornadiene 1, interesting example of imine-olefin homoconjugation, has been generated and spectroscopically characterized. Its instability is due to a retro-Diels-Alder reaction which generates cyclopentadiene and hydrogen cyanide.

An Improved Synthesis of 1α-hydroxy Vitamin D3

The efficient and stereoselective introduction of the 1α-OH function in vitamin D3 is described starting from the known previtamin D3 adduct 6.The sequence involves the stereoselective allylic bromination to 9, followed by substituti