30082-50-9

Upstream product

• 54563-03-0 C₂₇H₂₀N₂O 
• 622-37-7 Phenyl azide 
• 2556-46-9 N,N'-diphenylbenzamidine 
• 62-53-3 aniline 
• 100-52-7 benzaldehyde 
• 14062-91-0 (N-benzoyl-anilino)-phenyl-acetonitrile 
• 98-88-4 benzoyl chloride 
• 4553-59-7 2-anilino-2-phenylacetonitrile 
• 80577-80-6 9-Phenyl-6b,8,9,9a-tetrahydro-acenaphtho[1,2-d]oxazole 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 72867-52-8 5-imino-2,3,4-triphenyl-1,3-oxazolinium fluoroborate 
• 76677-97-9 7,8,9,10-Tetrachlor-2,5-imino-2,3,5,11-tetraphenyl-2,3,4,5-tetrahydro-1,6,3-benzodioxazocin-4-on 
• 968-02-5 2,3-trans-1,2,3-triphenylaziridine 

Relevant academic research and scientific papers

Reactions of cobaltacyclopentadiene complexes with organic azides directed toward synthesis of highly substituted pyrroles

The reactions of the cobaltacyclopentadiene complexes (η5-C5H5)(PPH3)-Co(-CR1=CR2-CR3=CR4)- (I) with organic azides were investigated.The complex Ia (R1)=R2=R3=R4=Ph) reacts with phenyl azide at 80 degC to give 1,2,3,4,5-pentaphenylpyrrole in 73percent yeld.Similarly, the reactions of Ia with benzoyl and t-butoxycarbonyl azides give 1-benzoyl- and 1-(t-butoxycarbonyl)-2,3,4,5-tetraphenylpyrroles in 41 and 64percent yields, respectively, but reaction with p-toluenesulfonyl azide gives 2,3,4,5-tetraphenylpyrrole and 3,4,5,6-tetraphenylpyridazine in 35 and 45percent yields, respectively, in place of the expected 1-(p-toluenesulfonyl)-2,3,4,5-tetraphenylpyrrole.The reaction of Ic (R1=R4=Ph, R2=R3=CO2CH3) with phenyl azide at 130 degC gives 1,2,5-triphenyl-3,4-bis(methoxycarbonyl)pyrrole (IIc)and 2,5-diphenyl-3,4-bis(methoxcarbonylpyrrole (Vb) in 22 and 15percent yields, respectively.The reaction of Ic with benzenesulfonyl azide gives only Vb in 57percent yield.In the reaction of Id (R1=R3=Ph, R2=R4=CO2CH3) with benzenesulfonyl azide, Vb was unexpectedly obtained in 26percent yield, together with 2,4-diphenyl-3,5-bis(methoxycarbonyl)pyrrole (Vc, 30percent), which suggests that a skeletal rearrangement of the metallacycle IXd to IXc occurs during the reaction.The reaction of Ic or Id with benzoyl azide at 130 degC gives the 2(1H)-pyridinone derivatives VIIIa (82percent) and VIIIb (53percent), which are the products of the reaction of the corresponding cobaltacyclpentadiene with phenyl isocyanate generated by the rearrangement of benzoyl nitrene, in place of the expected, corresponding pyrrole.

PHOTOFRAGMENTATION OF OXAZOLIDINES. A NEW METHOD FOR THE GENERATION OF AZIRIDINES

Irradiation of 4,5-cis-2,3,4,5-tetraaryloxazolidines and 3-aryl-3a,9b-dihydro-acenaphthoxazolidines generates the corresponding aziridine intermediates with elimination of aldehyde formed by fission of the C2-O and C4-C5 bonds in the former and the C2-O and C2-N bonds int the latter, respectively.The intervention of aziridine intermediates was proved by photo-cycloadditions.

Reactions of Five-membered Mesoionic Heterocycles with o-Quinonoid Compounds, III. - Thermal Cycloaddition Reactions with 1,3-Diazolium-4-olates and a 1,3-Oxazolium-4-olate

1,3-Diazolium-4-olates 6 and 3-methyl-5-(4-nitrophenyl)-1,3-oxazolium-4-olate (7) react with tetrachloro-o-benzoquinone (3) and N,N-diphenylsulfonyl-4,5-dimethyl-o-benzoquinone diimine (4), respectively, to give cycloadducts 10, 11, 12.The structure of 10b was determined by X-ray crystallography.

Synthetic Uses of Open-Chain Analogues of Reissert Compounds

Open-chain analogues, 2, of Reissert compounds are readily obtained by reaction of cyanohydrins with primary amines, the resulting aminonitriles, 1, then being acylated.Hydrofluoroborate salts, 3, of 2 are prepared by reaction with fluoroboric acid in glacial acetic acid.The salts, 3, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with ethyl acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction.The open-chain Reissert analogues 2 also undergo base-catalyzed reactions, such as alkylation to provide compounds 22, which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones 23.A conjugate addition reaction of the anion 18 to methyl acrylate to give, after some subsequent steps, a substituted pyrrole, 9, has also been demonstrated. α-Anilino ketones 27 result when the anion 18 is caused to react with aldehydes, the initial reaction mixtures being subjected to subsequent alkaline hydrolysis.Finally, N-benzyl Reissert analogues have been found to give desoxybenzoins plus benzonitriles on treatment with sodium hydride in tetrahydrofuran.