Category: 2451-91-4

Melekhova, Anna A. published the artcileTris(3,5-dimethylpyrazolyl)methane copper(I) complexes featuring one disubstituted cyanamide ligand, Name: N,N-Dibenzylcyanamide, the publication is Inorganica Chimica Acta (2019), 69-74, database is CAplus.

The complexes [Cu{HC(3,5-Me₂pz)₃}(NCNR₂)][BF₄] (1-8; R₂ = Me₂ 1, Et₂ 2, C₅H₁₀ 3, C₄H₈O 4, C₄H₈ 5, C₃H₆C₆H₄ [NC₃H₆C₆H₄ is 1,2,3,4-dihydroisoquinoline-2-yl] 6, (CH₂Ph)₂ 7, (Me)Ph 8) were prepared by the reaction of [Cu(NCMe)₄][BF₄] with HC(3,5-Me₂pz)₃ and NCNR₂ (CH₂Cl₂, 20-25°) and these species were characterized by C, H, N analyses, high resolution mass-spectrometry with electrospray ionization, ¹H, ¹³C{¹H} NMR and FTIR spectroscopic techniques, molar conductivity measurements, TG/DTA, and also by single-crystal x-ray diffraction for 3. The theor. topol. anal. of the electron d. distribution (QTAIM method) together with the NBO anal. were applied to study the nature of Cu-N and Cu-C coordination bonds in [Cu{HC(3,5-Me₂pz)₃}(NCNMe₂)]⁺, [Cu{HC(3,5-Me₂pz)₃}(NCMe)]⁺, and [Cu{HC(3,5-Me₂pz)₃}(CNMe)]⁺ model species. The nature of Cu-N coordination bonds in [Cu{HC(3,5-Me₂pz)₃}(NCNMe₂)]⁺ and [Cu{HC(3,5-Me₂pz)₃}(NCMe)]⁺ is very similar, whereas Cu-C contact in [Cu({HC(3,5-Me₂pz)₃})(CNMe)]⁺ is relatively more covalent. The calculated vertical total energies for the Cu-N and Cu-C coordination bonds cleavage increase in the following row: [Cu{HC(3,5-Me₂pz)₃}(NCMe)]⁺ (36 kcal/mol) < [Cu{HC(3,5-Me₂pz)₃}(NCNMe₂)]⁺ (41 kcal/mol) < [Cu{HC(3,5-Me₂pz)₃}(CNMe)]⁺ (47 kcal/mol), and these theor. data are coherent with the exptl. observations.

Inorganica Chimica Acta 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, Name: N,N-Dibenzylcyanamide.

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

Melekhova, Anna A. published the artcileA novel family of homoleptic copper(I) complexes featuring disubstituted cyanamides: a combined synthetic, structural, and theoretical study, Category: amides-buliding-blocks, the publication is New Journal of Chemistry (2017), 41(23), 14557-14566, database is CAplus.

The homoleptic Cu(I) complexes [Cu(NCNRR’)₄](BF₄) (R/R’ = Me/Me 1, Et/Et 2, C₅H₁₀ 3, C₄H₈O 4, C₄H₈ 5, C₃H₆C₆H₄ 6, CH₂Ph/CH₂Ph 7, Me/Ph 8) featuring disubstituted cyanamides were obtained in excellent (92-97%) yields by the reaction of [Cu(NCMe)₄](BF₄) and 4 equiv of NCNRR’. 1–8 Were characterized by at. absorption spectrometry (Cu%), high resolution ESI⁺-MS, molar conductivities, TG/DTA, and ¹H, ¹³C{¹H} NMR, FTIR spectroscopic techniques, and (1,3,4) by single-crystal x-ray diffraction. Results of DFT calculations and x-ray structure determinations reveal that equilibrium geometries of [Cu(NCMe)₄]⁺ and [Cu(NCNMe₂)₄]⁺ in the gas phase are normal tetrahedral (T_d) and significantly distorted, resp. Effects of crystal packing influence the values of the Cu-N-C angles in [Cu(NCNRR’)₄]⁺, which points out to the noticeable contribution of the heterocumulene mesomeric form for the dialkylcyanamide Cu(I) complexes. The QTAIM and NBO analyses indicate that relatively weak Cu-N contacts (15-31 kcal mol^-1) in both cases exhibit single bond character and clearly polarized toward the N atom (by 91-95%). The CDA shows that the {M} ← L σ-donation substantially prevails over the {M} → L π-back-donation in both [Cu(NCMe)₄]⁺ and [Cu(NCNMe₂)₄]⁺. The orbital, charge, and vibrational frequency arguments as well as inspection of the FTIR data suggest that the electrophilic activation of the N=C group in homoleptic nitrile and dialkylcyanamide Cu(I) complexes is similar, and the different behavior of nitriles and cyanamides in the 1,3-dipolar cycloaddition of ketonitrones is mainly due to the difference in the at. charges.

New Journal of 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 C15H14N2, Category: amides-buliding-blocks.

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

Spahn, Nathan A. published the artcileRegioselective Iron-Catalyzed [2 + 2 + 2] Cycloaddition Reaction Forming 4,6-Disubstituted 2-Aminopyridines from Terminal Alkynes and Cyanamides, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Journal of Organic Chemistry (2017), 82(1), 234-242, database is CAplus and MEDLINE.

Fe complexes bound by redox-active pyridine dialdimine (PDAI) ligands catalyze the cycloaddition of two terminal alkynes and one cyanamide. The reaction is both chemo- and regioselective as only 4,6-disubstituted-2-aminopyridine products are formed in moderate to high yields. Isolation of a Fe-azametallacycle (4) suggests catalyst deactivation occurs with large excess of cyanamide over longer reaction times. Fe-catalyzed cycloaddition allowed for a straightforward synthesis of a variety of amino-pyridines, including known estrogen receptor ligands.

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 C9H8BNO2, Recommanded Product: N,N-Dibenzylcyanamide.

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

Andreichikov, Yu. S. published the artcileChemistry of oxalyl derivatives of methyl ketones. XXXVIII. [4_π + 2_π]-Cycloaddition of aroylketenes at the CN bond of N-cyanoamines and phenyl cyanate, Application of N,N-Dibenzylcyanamide, the publication is Zhurnal Organicheskoi Khimii (1984), 20(8), 1755-9, database is CAplus.

Heating furandiones I, R = H, Me, Cl, EtO, Br, MeO) gave intermediate Ketenes p-RC₆H₄COCH:CO which cyclize with R¹CN to give oxazinones II (R² = R³ = Et, allyl, Bu, PhCH₂; R² = Me, R³ = Ph), III and IV. Reaction of I (R = H) with o-ClC₆H₄NHCN gave oxazolidinone V.

Zhurnal Organicheskoi Khimii 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 of N,N-Dibenzylcyanamide.

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

Stolley, Ryan M. published the artcileNickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides, SDS of cas: 2451-91-4, the publication is European Journal of Organic Chemistry (2011), 2011(20-21), 3815-3824, database is CAplus and MEDLINE.

A variety of bicyclic N,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in good to excellent yields. E.g., in presence of Ni(cod)₂ and IMes [1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene], [2+2+2] cycloaddition of MeCCCH₂C(CO₂Me)₂CH₂CCMe and N-cyanopyrrolidine gave 98% 2-aminopyridine derivative I. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermol. version employing 3-hexyne and N-cyanopyrrolidine also afforded the desired N,N-disubstituted 2-aminopyridine in good yield.

European 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 C5H7N3S3, SDS of cas: 2451-91-4.

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

Ayres, James N. published the artcileN-Cyanation of Secondary Amines Using Trichloroacetonitrile, Category: amides-buliding-blocks, the publication is Organic Letters (2016), 18(21), 5528-5531, database is CAplus and MEDLINE.

A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biol. active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.

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, Category: amides-buliding-blocks.

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

Wu, Yong-qian published the artcile1-Cyanoimidazole as a Mild and Efficient Electrophilic Cyanating Agent, Formula: C15H14N2, the publication is Organic Letters (2000), 2(6), 795-797, database is CAplus and MEDLINE.

A mild and high-yielding cyanating reaction of amine, sulfur, and carbanion nucleophiles, e.g., PhNH₂, (PhCH₂)₂NH, PhCCH, PhCH₂SH, is reported which uses 1-cyanoimidazole as an electrophilic cyanating agent to give the corresponding cyanated products, e.g., PhNHCN, (PhCH₂)₂NCN, PhCCCN, PhCH₂SCN.

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 C5H5BO5, Formula: C15H14N2.

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

Wu, Y.-Q. published the artcileCyanogen halides, cyanates and their sulfur, selenium, and tellurium analogues, sulfinyl and sulfonyl cyanides, cyanamides, and phosphaalkynes, Related Products of amides-buliding-blocks, the publication is Science of Synthesis (2005), 17-63, database is CAplus.

A review of the preparation of cyanogen halides and cyanates as well as their application to organic synthesis. Sulfur, selenium, and tellurium analogs, sulfinyl and sulfonyl cyanides, cyanamides, and phosphaalkynes are included.

Science of 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 C9H9F5Si, Related Products of amides-buliding-blocks.

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

Schindler, Norbert published the artcileReactions with dialkylcyanamides. Reaction of dialkylcyanamides with sulfur or phosphorus halides. Synthesis of substituted chloroformamidines, Application of N,N-Dibenzylcyanamide, the publication is Chemische Berichte (1973), 106(1), 56-61, database is CAplus.

Reaction of R2NCN (R = Et, PhCH2, cyclohexyl; R2N = piperidino) with SCl2 (or SOCl2), SO2Cl2, and P(X)Cl3 (X = O or S) yielded ≤90% (R2NCCl:N)2S+Cl Cl-, ≤100% R2NCCl:NSO2Cl, and ≤87% R2NCCl:NP(X)Cl2, resp. The compounds obtained were characterized by the ir spectra.

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 of N,N-Dibenzylcyanamide.

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

Misner, Jerry W. published the artcileAn improved method for the decyanation of N,N-disubstituted cyanamides, Synthetic Route of 2451-91-4, the publication is Journal of Organic Chemistry (1987), 52(14), 3166-8, database is CAplus.

The cleavage of N,N-disubstituted cyanamides, e.g. the ergoline I (R = cyano), to secondary amines, e.g. I (R = H), is effected rapidly and in high yields with NaOH or KOH in ethylene glycol at temperature greater than 120°. The products can usually be isolated easily as either the free amines or as their salts so long as they are reasonably hydrophobic. This procedure is an excellent alternative to other methods, especially with acid sensitive substrates.

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 C15H14N2, Synthetic Route of 2451-91-4.

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