2513-64-6

Upstream product

• 50-00-0 formaldehyd 
• 150-61-8 N,N'-diphenylethylenediamine 
• 779-52-2 1-phenyl-2-piperidin-1-yl-ethanone 
• 728-24-5 1,3-diphenyl-2-imidazolidone 
• 2179-89-7 bis(1,3-diphenyl-2-imidazolidinylidene) 
• 2522-21-6 4,5-Dihydro-1,3-diphenyl-1H-imidazoliumchlorid 
• 75681-30-0 1-(4-methoxyphenyl)-2-(methyl(phenyl)amino)ethan-1-one 
• 76007-17-5 2-N-methylanilinoacetylfuran 
• 76007-22-2 2,4-dimethyl-5-N-methylanilinoacetylthiazole 
• 76007-18-6 2-N-methylanilinoacetylbenzofuran 
• 86453-45-4 1,3-diphenyl-2-imidazolidineselenone 
• 98-86-2 acetophenone 
• 193552-63-5 2-cyano-1,3-diphenylimidazolidine 
• 96-22-0 pentan-3-one 

Downstream Products

• 55055-34-0 N-formyl-N,N'-diphenylethylenediamine 
• 150-61-8 N,N'-diphenylethylenediamine 
• 13375-83-2 N¹,N¹,N²,N²-tetraphenylethane-1,2-diamine 
• 1687-58-7 1,3-diphenyl-2-imidazolidinethione 

Relevant academic research and scientific papers

Heterocyclic spirocyclohexadienones, I

The compound formerly described as methylene amine 3 is in fact the heterocyclic spirocyclohexadienone 9. Contrary to literature, catalytic hydrogenation does not lead to methylamine 4 but to spiroketone 10 and a mixture of diastereomeric spirocyclic alco

Bridging amines with CO2: Organocatalyzed reduction of CO2 to aminals

The four-electron reduction of CO2 in the presence of secondary aromatic amines is described for the first time to access aminals. Under metal-free hydrosilylation conditions, the four C-O bonds of CO2 are cleaved, and the organocatalysts are able to balance the reactivity of CO2 to promote the selective formation of two C-N and two C-H bonds. The methodology enables the formation of various symmetrical and unsymmetrical aminals.

A general catalytic methylation of amines using carbon dioxide

Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright

C-H activation with elemental sulfur: Synthesis of cyclic thioureas from formaldehyde aminals and S8

The C-H activation of cyclic formaldehyde aminals LCH2 (L = RNCH2CH2CH2-NR and RNCH2CH2-NR, R = Me, Et, iPr, tBu, or Ph) with S8 proceeds at unusually low temperatures (T 2S. The reaction constitutes a new, solvent-free method for the synthesis of thioureas that eliminates the toxic and highly flammable CS2. For R = tBu, the ionic carbenium thiocyanates [LCH]+ SCN- dominate the product spectrum and the respective thioureas are obtained in low yield. The reactivity of the analogous sulfur and oxygen ring systems towards S8 was investigated. 1,3-Dithiolane is cleanly converted into 1,3-dithiolane-2-thione (S8, 14 d, 190°C) and resembles the cyclic formaldehyde aminals in this respect. 1,3-Dioxolane (L = OCH2CH2O) is completely inert towards sulfur even under forceful reaction conditions (190°C, 14 d). The formation of thioureas from aminals was investigated at the CBS-4 and B3LYP/6-31G(d) levels of theory.

Nucleophilic Addition to Substituted 1H-4,5-Dihydroimidazolium Salts

1H-4,5-Dihydroimidazolium salts 1 react readily with nucleophilic reagents originating cyclic products which may be stable or become transformed into acyclic compounds maintaining the structural ethylenediamine unit. With methylmagnesium iodide compound le affords the expected imidazolidine, but in the case of substituted 1-aryl-3-methyl-2-phenyl salts 1b-d the N-aryl-N'-methylethylenediamines 3b-d and acetophenone (4) were isolated, the process representing the transfer of the C-2 unit to a nucleophilic carbon. With alkaline cyanides salts 1 react efficiently affording α,α-diaminonitriles 5. In these compounds the cyano group may be readily substituted by nucleophiles (hydroxyl anion, species with nucleophilic carbon and reagents that act by hydride ion transfer), in a way similar to the salts but with better yields.

Reduction of Substituted 1H-4,5-Dihydroimidazolium Salts

Reactions of several substituted 1H-4,5-dihydroimidazolium salts 1 with nucleophilic and electrophilic reducing agents acting via hydride transfer were explored.Reaction of compounds 1 with lithium aluminum hydride in THF afforded the corresponding imidazolidines 2.When alkaline borohydrides (sodium borohydride, potassium borohydride, sodium cyanoborohydride) in ethanol at room temperature were used, partial or total over-reduction of compounds 2 leading to N,N,N'-trisubstituted ethylenediamines took place on occasion.Results may be explained taking into account that reductive cleavage of 2 proceeds via a stabilized iminium ion present in protic solvents.Treatment of compounds 1 with an excess of borane in THF afforded the corresponding imidazolidines 2 or their borane complexes, according to the substituent type.

A Stereochemical Investigation of 1,3-Diphenyl-4-methyl-1,3-diazolidines and its Related Compounds via NMR

Four 1,3-diphenyl-4-methyl-1,3-diazolidines and two isomeric 2,5-diphenyl-3-methyl-1,2,5-thiadiazolidine 2-oxides were prepared.The pmr and cmr spectra of these compounds were obtained.On the basis of the chemical shifts due to the γ- and δ-effects, the stereochemical structures are discussed.

Synthesis of 1,3-Disubstituted Diazolidines

Symmetrical and unsymmetrical 1,3-diaminoethanes 1 are obtained by the reduction of N,N'-disubstituted oxamides 4 with lithium aluminum hydride.The oxamides 4 are readily produced by treatment of diethyl oxalate with primary amines.The 1,3-diaminoethanes 1 lead to 1,3-diazolidines 2 on treatment with formaldehyde.

Reduction of Cyclic Ureas with Lithium Aluminum Hydride

A series of 1,3-dialkyl-2-imidazolidinones 1 and 1,3-dialklyltetrahydro -2(1H)-pyrimidinones 2 were reduced to the corresponding aminals 3 and 4, respectively, when treated with excess lithium aluminum hydride in ether.The rate of reduction is affected dr