2645-39-8Relevant academic research and scientific papers
Crystal structure, ab initio calculations and fingerprint plots of a new polymorph of N′,N″,N?-triphenylbiuret
Pereira Silva, Pedro S.,Ghalib, Raza Murad,Mehdi, Sayed Hasan,Hashim, Rokiah,Sulaiman, Othman,Silva, Manuela Ramos
, p. 66 - 71 (2011)
A new polymorph of N′,N″,N?-triphenylbiuret, C 20H17N3O2 (form II), has been synthesized and the structure has been solved by X-ray diffraction. The crystals are monoclinic, space group P21/c, with a
Carbon-carbon bond formation between a diferra(μ-alkylidene)carbene complex and an isocyanate RNCX(R = Et, Ph; X = O, S). X-ray structure of 2-MeCC(NEt)2CONR>>
Crocq, Veronique,Daran, Jean-Claude,Jeannin, Yves
, p. 85 - 98 (1989)
The major products from the reaction of 2-MeCC(NEt2)>> (1) with isocyanates and isothiocyanate RNCX were the binuclear complexes 2-MeCC(NEt2)CXNR>>containing a ferrapyrrolidone fragment (2: X = O, R = Et; 3: R = Ph; 4: X = S, R = Ph).Compounds 2 and 3 were characterized by X-ray diffraction studies.Complex 4 was characterized by IR, 1H NMR, and mass spectrometry.Crystal data for 2: monoclinic, space group P21/a, a 13.079(2), b 11.436(2), c 13.544(2) Angstroem, β 94.21(1)o, V 2020 (Angstroem)3, Z = 4, Rw = 0.0281 for 2348 reflexions.Crystal data for 3: triclinic, space group P1, a 9.326(1), b 1 0.786(1), c 12.145(2) Angstroem, α 75.39(1)o, β 80.59(1)o, 76.75(1)o, V 1143 (Angstroem)3, Z = 2, Rw = 0.0313 for 2703 reflexions.They contain two Fe(CO)3 fragment linked by a metal-metal bond and bridged by the MeC=C(NEt2)CONR ligand, which is derived from the combination of the isocyanate ligand with the aminoalkyne CH3CCNEt2 in 1.
Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C-H Amidation of 2-Phenylpyridine with Arylisocyanates
Altalhi, Weam A. O.,Canty, Allan J.,Czyz, Milena L.,Donnelly, Paul S.,McInnes, Lachlan E.,McKay, Alasdair I.,O'Hair, Richard A. J.
, p. 2680 - 2687 (2020/03/13)
The Ru(II)-catalyzed amidation of 2-Arylpyridines with aryl isocyanates via C-H bond activation is less efficient than described previously, due to the formation of a series of side products, which were readily identified using direct infusion electrospray mass spectrometry and high-performance liquid chromatography-mass spectrometry.
Iron(II)-Catalyzed Hydroamination of Isocyanates
South, Amy J.,Geer, Ana M.,Taylor, Laurence J.,Sharpe, Helen R.,Lewis, William,Blake, Alexander J.,Kays, Deborah L.
supporting information, p. 4115 - 4120 (2019/10/17)
A two-coordinate Fe(II) m-terphenyl complex acts as a precatalyst for the hydroamination of isocyanates, affording urea and biuret derivatives, with product selectivity accomplished via modification of the reaction conditions. Using a more nucleophilic amine facilitates the insertion of up to four isocyanates into the N-H bond, affording triuret and tetrauret derivatives.
One- or Two-Step Synthesis of C-8 and N-9 Substituted Purines
Bollier, Mélanie,Klupsch, Frédérique,Six, Perrine,Dubuquoy, Laurent,Azaroual, Nathalie,Millet, Régis,Leleu-Chavain, Natascha
, p. 422 - 430 (2018/02/19)
A novel and original strategy to obtain rapidly a large diversity of C-8 and N-9 substituted purines was developed. The present procedure describes annulation reactions in one or two steps starting from 5-aminoimidazole-4-carbonitriles 1-8 in moderate to good yields. 8,9-Disubstituted-6,9-dihydro-1H-purin-6-ones 9-14, 6-amino-8,9-disubstituted-3,9-dihydro-2H-purin-2-ones 15-20, 8,9-disubstituted-3,9-dihydro-2H-purin-2,6-diamines 21-24 and 6-imino-1-phenyl-8,9-disubstituted-6,9-dihydro-1H-purin-2-(3H)-ones 25-26 were synthesized in one step using formic acid, urea, guanidine carbonate, and phenylisocyanate, respectively, whereas 8,9-disubstituted-9H-purin-6-amines 27-31 and 6-imino-8,9-disubstituted-6,9-dihydro-1H-purin-1-amines 32-33 were obtained in two steps using formamide and hydrazine, respectively.
Reaction of organozinc halides with aryl isocyanates
Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
supporting information, p. 2588 - 2593 (2013/03/28)
Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
Reaction of 3-hydroxyquinoline-2,4-diones with isocyanates and thermally induced transformation of the reaction products
Mrkvicka, Vladimir,Lycka, Antonin,Vicha, Robert,Klasek, Antonin
experimental part, p. 78 - 91 (2011/03/16)
3-Hydroxyquinoline-2,4-diones 1 react with isocyanates to give novel 1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl (alkyl/aryl)carbamates 2 and/or 1,9b-dihydro-9b-hydroxyoxazolo[5,4-c]quinoline-2,4(3aH,5H)-diones 3. Both of these compounds are converted, by boiling in cyclohexylbenzene solution in the presence of Ph3P or 4-(dimethylamino)pyridine, to give 3-(acyloxy)-1,3-dihydro-2H-indol-2-ones 8. All compounds were characterized by IR, and 1H- and 13C-NMR spectroscopy, as well as by EI mass spectrometry. Copyright
Reactions of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene and 2-amino-3-cyano-4,7-diphenyl-5-methyl-4H-pyrano[2,3-c] pyrazole with phenylisocyanate, carbon disulfide, and thiourea
Youssef, Ahmed S.A.,Kandeel, Kamal A.,Fouli, Fouli A.,Abou-Elmagd, Wael S.I.
, p. 6 - 11 (2007/10/03)
2-Amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene 1a or 2-amino-3-cyano-4, 7-diphenyl-5-methyl-4H-pyrano[2,3-c]pyrazole 2a reacted with phenylisocyanate in dry pyridine to give 2- (3-phenylureido)-3-cyanobenzo[b] thiophene 1b or 2-disubstituted amino-3-
Synthesis and highly selective Diels-Alder cycloadditions of the new dienes N-substituted 2,3,5,6-tetrahydrobenzoxazol-2-ones
Martínez, Rafael,Jiménez-Vázquez, Hugo A.,Delgado, Francisco,Tamariz, Joaquín
, p. 481 - 492 (2007/10/03)
The synthesis of the new dienes N-substituted 2,3,4,5-tetrahydrobenzoxazol-2-ones 8a-8c is described, through a one-step convergent process from 1,2-cyclohexanedione (7a) and the corresponding isocyanates 2a-2c. The presence of electron-donor substituents in the aryl ring of the isocyanate gave rise to the exclusive formation of the captodative olefins 10. Diene 8a proved to be reactive and stereoselective in Diels-Alder additions with a cyclic olefin. The reaction with acetylenic dienophiles yielded the 2,3-dihydrobenzoxazol-2-ones 21 and 24, as the products of sequential [4+2] cycloaddition and retro-Diels-Alder reactions. Methyl vinyl ketone (22) underwent regio- and stereoselective tandem Diels-Alder and Michael additions to give propellane 29a. Evidence of an endo π-pyramidalization of the central double bond of adduct 19 would rationalize the exo stereoselection in the formation of 29a. The regioselectivity in these reactions has been rationalized in terms of FMO theory by ab initio calculations.
Selective Reactivity of sp3and sp2 Carbanions of 1-Substituted 1,2,4-Triazoles. A Comparative Approach
Katritzky, Alan R.,Darabantu, Mircea,Aslan, Diana C.,Oniciu, Daniela C.
, p. 4323 - 4331 (2007/10/03)
The regioselectivity of lithiation reactions of 1-n-alkyl-, 1-allyl-, and 1-propargyl-1H-1,2,4-triazoles was studied in terms of the products formed by sequential treatment with BuLi and a range of electrophiles.
