Category: 2451-91-4

Wang, Chunxiang published the artcileIron-Catalyzed Cycloaddition Reaction of Diynes and Cyanamides at Room Temperature, Formula: C15H14N2, the publication is Journal of Organic Chemistry (2013), 78(7), 3065-3072, database is CAplus and MEDLINE.

An iron-catalyzed [2+2+2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. E.g., in presence of FeI₂, dppp, and Zn dust, [2+2+2] cycloaddition reaction of MeCCCH₂NTsCH₂CCMe and (Me₂CH)₂NCN gave 91% 2-aminopyridine derivative (I). Insights toward the reaction process were investigated through in situ IR spectra and control experiments In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.

Journal of Organic Chemistry published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C8H5F3N4, Formula: C15H14N2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Fischer, Helmut published the artcileCoupling of cyanamides with a carbyne ligand – formation of η²-(C,N)-imidazolium complexes and ansa-carbene complexes, Application In Synthesis of 2451-91-4, the publication is Chemische Berichte (1993), 126(11), 2373-8, database is CAplus.

Dicarbonyl(cyclopentadienyl)(phenylcarbyne)manganese complexes [Cp(CO)₂MnCPh]⁺X^– (1–X) (X = BF₄, BCl₄) react with dimethyl-(2a), diethyl-(2b), and diisopropylcyanamide (2c) in five-fold excess by a head-to-tail cyclization of two cyanamides with the carbyne ligand to give η²-(C,N)-imidazolium complexes I. As byproducts ansa-amino(alkylideneamino)carbene complexes II are formed in which a N:C(Ph) group bridges the carbene carbon and the Cp ring. With increasing excess of the cyanamide the product ratio I:II increases. Among the products of the reaction of 1–X with the cyanamides NCNR₂ [NR₂ = N(isobutyl)₂, N(Bzl)₂, N(Me)Ph] no imidazolium complexes I are detected, only ansa-carbene complexes II are isolated. PMe₃/H₂O or pyridine/H₂O displaces the heterocyclic ligand from I (R = Me, X = BF₄). The structure of I (R = Me, X = BF₄) is established by an x-ray anal.

Chemische Berichte published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Application In Synthesis of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hang, Zhaojun published the artcileA practical method for N-cyanation of secondary amines and sulfonamides, Application In Synthesis of 2451-91-4, the publication is Tetrahedron Letters (2022), 153564, database is CAplus.

Cyanamides are an important class of mols. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1,2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl)-N-arylsulfonyl-cyanamides, as the significant building blocks of the organic transformation.

Tetrahedron Letters published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Application In Synthesis of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Rydfjord, Jonas published the artcileDecarboxylative Palladium(II)-Catalyzed Synthesis of Aryl Amidines from Aryl Carboxylic Acids: Development and Mechanistic Investigation, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Chemistry – A European Journal (2013), 19(41), 13803-13810, database is CAplus and MEDLINE.

A fast and convenient synthesis of aryl amidines starting from carboxylic acids and cyanamides is reported. The reaction was achieved by palladium(II) catalysis in a one-step microwave protocol using [Pd(O₂CCF₃)₂], 6-methyl-2,2′-bipyridyl, and trifluoroacetic acid (TFA) in N-methylpyrrolidinone (NMP), providing the corresponding aryl amidines in moderate to excellent yields. E.g., in this system, reaction of 2,4,6-trimethoxybenzoic acid and N-cyanopiperidine gave 96% amidine I. The protocol is very robust with regards to the cyanamide coupling partner but requires electron-rich ortho-substituted aryl carboxylic acids. Mechanistic insight was provided by a DFT investigation and direct ESI-MS studies of the reaction. The results of the DFT study correlated well with the exptl. findings and, together with the ESI-MS study, support the suggested mechanism. Furthermore, a scale-out (scale-up) was performed with a non-resonant microwave continuous-flow system, achieving a maximum throughput of 11 mmol h^-1 by using a glass reactor with an inner diameter of 3 mm at a flow rate of 1 mL min^-1.

Chemistry – A European Journal published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Recommanded Product: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zhong, Yao published the artcile3,5-Disubstituted 2-Aminopyridines via Nickel-Catalyzed Cycloaddition of Terminal Alkynes and Cyanamides, SDS of cas: 2451-91-4, the publication is Synlett (2015), 26(3), 307-312, database is CAplus.

The regioselectivity of the Ni/SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolidene] -catalyzed cycloaddition of terminal alkynes and cyanamides was explored. In general, 3,5-disubstituted 2-aminopyridines were formed as the major product.

Synlett published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C14H14, SDS of cas: 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Melekhova, Anna A. published the artcileCopper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: A Step toward Sustainable Generation of 2,3-Dihydro-1,2,4-oxadiazoles, HPLC of Formula: 2451-91-4, the publication is ACS Omega (2017), 2(4), 1380-1391, database is CAplus and MEDLINE.

Cu^I -catalyzed cycloaddition of the ketonitrones Ph₂C=N⁺ (R’)O^– (R’ = Me, CH₂Ph) to the disubstituted cyanamides NCNR₂ (R = Me₂ , Et₂ , (CH₂)₄ , (CH₂)₅ , (CH₂)₄O, C₉H₁₀, (CH₂Ph)₂ , Ph(Me)) gives corresponding 5-aminosubstituted 2,3-dihydro- 1,2,4-oxadiazoles (16 examples) in good to moderate yields. The reaction proceeds under mild conditions (CH₂Cl₂ , RT or 45 °C) and requires 10 mol% of [Cu(NCMe)₄](BF₄) as the catalyst. Somehow reduced yields are due to the individual properties of 2,3- dihydro-1,2,4-oxadiazoles, which easily undergo ring-opening via the N-O bond splitting. Results of the DFT calculations reveal that the cycloaddition of ketonitrones to Cu^I -bound cyanamides is a concerted process and the copper-catalyzed reaction is controlled by the predominant contribution of HOMO_dipole-LUMO_{dipolarophile} interaction (group I by the Sustmann’s classification). Metal-involving process is much more asynchronous and profitable from both kinetic and thermodn. viewpoints than the hypothetical metal-free reaction.

ACS Omega published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, HPLC of Formula: 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Rydfjord, Jonas published the artcileRoute to 3-Amidino Indoles via Pd(II)-Catalyzed C-H Bond Activation, Quality Control of 2451-91-4, the publication is Organic Letters (2017), 19(15), 4066-4069, database is CAplus and MEDLINE.

We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C-H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole-palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations, and a plausible reaction pathway is presented.

Organic Letters published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Quality Control of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Oae, Shigeru published the artcileNucleophilic substitution and elimination reactions on the nitrogen atom. Reaction of N,N-dibenzyl-O-p-nitrobenzoylhydroxylamine with various nucleophiles in dipolar aprotic solvents, Computed Properties of 2451-91-4, the publication is Chemistry Letters (1974), 621-4, database is CAplus.

The reactions of p-O2NC6H4CO2N(CH2Ph)2 (I) with NaN3, LiCl, NaBr, NaI, or NaOH in DMF or Me2SO gave Ph-CHO, PhCH2NH2, and p-O2NC6H4CO2- via an E2 mechanism. This was substantiated by kinetic isotope effects of 7.6 and 8.1for the reactions with N3- and Cl-, resp. The reaction of I with NaCN in Me2SO gave 8% PhCHO, 8% PhCH2NH2, 46% (PhCH2)2NCN, and ∼100% p-O2NC6H4CO2- in an SN2 reaction at the N atom.

Chemistry Letters published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Computed Properties of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bakunov, Stanislav A. published the artcileModification of the Tiemann rearrangement: One-pot synthesis of N,N-disubstituted cyanamides from amidoximes, SDS of cas: 2451-91-4, the publication is Synthesis (2000), 1148-1159, database is CAplus.

Amidoximes were converted to N,N-disubstituted cyanamides in 70-92% yield in a one-pot synthetic procedure by treating the amidoximes with tosyl chloride, followed by treatment with alkyl halide under phase-transfer conditions.

Synthesis published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, SDS of cas: 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kaye, Irving Allan published the artcilePreparation of secondary and tertiary 2-thiazolylamines, Computed Properties of 2451-91-4, the publication is Journal of the American Chemical Society (1952), 2271-3, database is CAplus.

cf. C.A. 46, 9094b. Basically mono- or disubstituted derivatives of 2-aminothiazole (I) were prepared by the condensation of an appropriately substituted thiourea with di-Me chloroacetal (II). The reaction of 2-bromothiazole (IIA) with either a primary or secondary amine was a less satisfactory method. N,N-Diethyl-N’-benzyl-N’-(2-thiazolyl)ethylenediamine (III), tested for antihistaminic activity on the isolated guinea-pig ileum strip, showed 1.5% of the activity of pyribenzamine (IV). The N,N-di-Me analog (V) of III was 20% as active as IV. Against acetylcholine, V had 0.15% the activity of atropine. The method of Ganapathi and Venkataraman (C.A. 40, 4059.5) gave 67% IIA. The method of Campbell, et al. (C.A. 43, 1340g), gave 93% PhCH:NEt (VI). VI with Pd-C gave 94% PhCH₂NHEt (VII), b₈₂ 124-5°. The method of Moore and Crossley (Organic Syntheses, 21, 81(1941); C.A. 35, 6241.4) yielded 91 and 89%, resp., of PhCH₂NCS, b₃ 105-7°, and EtNCS, b₁₂₀ 60-70°. The method of Frank and Smith (Ibid. 28, 89(1948); C.A. 43, 1734h) yielded 71% BzNHCSNHCH₂Ph (VIII), m. 124-4.5°. Alk. cleavage of VIII gave 92% H₂NCSNHCH₂Ph (IX). PhCH₂NCS and NH₄OH gave IX. EtNCS and NH₄OH gave 70% EtNHCSNH₂. The method of Frank and Smith, loc. cit., gave 79.5% BzNHCSN(CH₂Ph)₂ (X), m. 142-3°. Et₂NCH₂CH₂NHCH₂Ph (XI) (82.5 g.) in 100 cc. C₆H₆ added dropwise (cooling) to 21.2 g. BrCN in 100 cc. C₆H₆, the solution heated 4 h. on the steam bath, cooled, treated with 20 g. NaOH in 150 cc. water, extracted with C₆H₆, and the extract fractionated yielded 37.1 g. XI, b₅ 128-34°; and 41.3 g. benzyl(2-diethylaminoethyl)cyanamide (XII), b₅ 179-80°. The same procedure, except for filtration of the HBr salts of excess amines, yielded 95% NCNEtCH₂Ph (XIII), b₁₂ 157-8°; and 100% NCN(CH₂Ph)₂ (XIV), m. 60-2°, b₃ 180-5°. Gaseous NH₃ and H₂S passed rapidly into 17.6 g. XIII in 125 cc. MeOH saturated with NH₃ (temperature held below 35°), the flow of NH₃ stopped after 1 h., that of H₂S 1 h. later, ice and water added, and the precipitate filtered yielded 15.8 g. PhCH₂EtNCSNH₂, m. 122.5-3.5°. XIV yielded 73% (PhCH₂)₂NCSNH₂. XII gave an oil which was cyclized in 45% yield to III, b_0.9 135-9°, m. 147.5-8.5°. V, 34% yield, b_0.04 118-25°, m. 158.5-9.5°. Method A: PhCH₂NHCSNH₂ (74.8 g.), 67.3 g. II, and 250 cc. water heated 18 h. on the steam bath, diluted with 1 l. water, and made alk. with NaOH yielded 80.0 g. 2-benzylaminothiazole (XV), m. 126-7.5°. IIA (16.4 g.) and 21.4 g. PhCH₂NH₂ refluxed 72 h. in cumene or xylene yielded 1.8 g. XV, m. 127.5-8.5. B: IIA (8.2 g.), 11.6 g. Et₂NCH₂CH₂NH₂, and 12 g. pyridine refluxed 3.5 h., cooled to room temperature, 100 cc. water added, and the solution saturated with K₂CO₃ and extracted with Et₂O yielded 6.0 g. N,N-diethyl-N’-(2-thiazolyl)ethylenediamine, b_0.4 112-15°; di-HCl salt, m. 181.5-2.5°. The following N,N-disubstituted 2-aminothiazoles were also prepared (substituents, method, b.p./mm., % yield, and m.p. given): Et, H, A, -, 70, 49-50° (picrate, m. 182-3°); Et, benzyl, A, 119-22°/0.10, 28, 153.5-54°; benzyl, benzyl, A, 116-20°/0.05, 57, 167-7.5°.

Journal of the American Chemical Society published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Computed Properties of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics