72709-29-6

Upstream product

• 538-51-2 benzylidene phenylamine 
• 109-64-8 1,3-dibromo-propane 
• 56139-59-4 4-oxo-4-phenyl-butyraldehyde 
• 98-95-3 nitrobenzene 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 62-53-3 aniline 
• 118575-70-5 trans-styrylacetyl chloride 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 4096-21-3 N-phenylpyrrolidine 
• 591-50-4 iodobenzene 
• 244016-00-0 N-[(3E)-4-phenyl-3-buten-1-yl]benzenamine 

Downstream Products

• 18328-11-5 3-benzyl propionaldehyde 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Iron-Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines such as piperidines and azepanes were efficiently synthesized with yields up to 92%, by reaction of anilines with 1,5- or 1,6-keto acids, respectively. Similarly, N-arylinsolidoline compounds can be prepared from 2-formylbenzoic acid in 57–93% yields. (Figure presented.).

Triphenylphosphine-N-bromosuccinimide mediated chemoselective cyclodehydration of diols

A triphenylphosphine-N-bromosuccinimide mediated chemoselective cyclodehydration of diols is presented for the synthesis of polysubstituted tetrahydrofurans. 1,4-Diols and their derivatives can be rapidly cyclized to furnish tetrahydrofurans in high yields with one equivalent of Ph3P/NBS. Higher amount of Ph3P/NBS leads to the formation of dibromobutanes.

Ruthenium-porphyrin-catalyzed diastereoselective intramolecular alkyl carbene insertion into C-H bonds of alkyl diazomethanes generated in situ from N-tosylhydrazones

With a ruthenium-porphyrin catalyst, alkyl diazomethanes generated in situ from N-tosylhydrazones efficiently underwent intramolecular C(sp3)-H insertion of an alkyl carbene to give substituted tetrahydrofurans and pyrrolidines in up to 99% yield and with up to 99:1 cis selectivity. The reaction displays good tolerance of many functionalities, and the procedure is simple without the need for slow addition with a syringe pump. From a synthetic point of view, the C-H insertion of N-tosylhydrazones can be viewed as reductive coupling between a C=O bond and a C-H bond to form a new C-C bond, since N-tosylhydrazones can be readily prepared from carbonyl compounds. This reaction was successfully applied in a concise synthesis of (-)-pseudoheliotridane.

Selective and catalytic arylation of N-phenylpyrrolidine: sp3 C-H bond functionalization in the absence of a directing group

We herein describe our studies on arylation of N-phenylpyrrolidine, which led to the development of a new transformation for the direct and selective arylation of sp3 C-H bonds in the absence of a directing group. In this method, Ru(H)2(CO)(PCy3)3 4 was used as the catalyst, and preliminary mechanistic studies suggested that Ru(Ph)(I)(CO)(PCy3)2 5 is the key intermediate of the catalytic cycle. A large kinetic isotope effect (kH/kD = 5.4) was observed, which supports the proposal that C-H bond metalation is the slow step. Preliminary examination of the substrate scope showed that in addition to N-phenylpyrrolidine, N-methyl- and N-benzylpyrrolidine, as well as N-benzoylpyrrolidine, were arylated under the reaction conditions. Copyright

N-phenyl-substituted pyrrolidines, piperidines and azabicyclics by a tandem reduction-double reductive amination reaction

N-Phenyl-substituted pyrrolidines and piperidines have been synthesized by catalytic reduction of nitrobenzene in the presence of 4- and 5-oxoaldehydes, respectively. The process involves reduction of the aromatic nitro group to give the N-phenylhydroxylamine or aniline followed by reductive amination with the two carbonyl functional groups. Monocyclic systems are generally formed in high yield and are easily purified. The method has also been extended to the synthesis of fused N-phenylazabicyclics from 2-(3-oxopropyl)cycloalkanones. A high degree of diastereoselectivity for the trans-fused product is observed in substrates having an ester group α to the cycloalkanone carbonyl. Bicyclic precursors lacking this ester group give mixtures of cis and trans products. Finally, contrary to previous reports, we have demonstrated that aniline can be substituted for nitrobenzene in these reactions.

Formation of pyrrolidines by the titanocene(II)-promoted intramolecular reaction of N-[3,3-bis(phenylthio)propyl]anilides

The reaction of anilides with the titanium carbene complexes generated by the desulfurization of thioacetals with the titanocene(II) species Cp2Ti[P(OEt)3]2 produced the corresponding enamines. Unusual formation of pyrroli

Formation and behavior of intramolecular N-(styrylalkyl)aniline exciplexes

The photophysical and photochemical behavior of several aniline spacer - styrene molecules in which the spacer is a short polymethylene chain has been investigated. Long wavelength excitation selectively excites the aniline chromophore which undergoes intramolecular quenching by the styrene to yield an intramolecular exciplex. Exciplex fluorescence is observed for both of the tertiary anilines investigated and for one of the three secondary anilines. More rapid exciplex formation in nonpolar vs. polar solvents is attributed to the necessity of desolvating the polar aniline singlet in polar solvents. Intramolecular adduct formation is the major photochemical process for the secondary anilines, but is highly inefficient for the tertiary anilines. The behavior of the intramolecular aniline-styrene exciplexes is compared to that of the styrene-amine exciplexes previously investigated in this laboratory.

One-step Synthesis of Cyclic Compounds by Electrochemical Reduction of Unsaturated Compounds in the Presence of Dielectrophiles

The one-step synthesis of cyclic compounds is achieved in a few cases by electroreduction of unsaturated compounds in DMF, at a mercury pool cathode, in the presence of a more difficulty reducible dielectrophile.Unsaturated compounds include activated olefins, aromatic Schiff bases, ketones, and azo, nitroso, and nitro compounds.Four dielectrophiles are used; they are tri- or tetramethylene bromide, succinyl chloride, and 4-bromobutyryl chloride.The electrochemical synthesis of derivatives of cyclohexane, piperidine, pyrrolidine, hexahydropyridazine, tetrahydropyridazinone, tetrahydropyridazinedione, tetrahydrooxazine, isoxazolidine, and spirolactone can be succesfully performed.Their yields range from 8 to 78percent depending on competitive reactions.Results of chemical reduction by alkali metals and electrochemical reduction are compared.