16776-73-1Relevant articles and documents
NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N?O bond formation
Li, Ertong,Wang, Manman,Wang, Zhen,Yu, Wenquan,Chang, Junbiao
, p. 4613 - 4618 (2018/07/31)
A reaction involving an efficient NBS-mediated oxidative N?O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild re
A metal-free tandem approach to prepare structurally diverse N-heterocycles: Synthesis of 1,2,4-oxadiazoles and pyrimidinones
Gupta, Puneet K.,Hussain, Mohd. Kamil,Asad, Mohd.,Kant, Ruchir,Mahar, Rohit,Shukla, Sanjeev K.,Hajela, Kanchan
, p. 3062 - 3070 (2014/07/07)
A metal-free one-pot approach to the diversity oriented synthesis of N-heterocycles, 1,2,4-oxadiazoles and 2,6 disubstituted pyrimidin-4-ones is described via carboxamidation of amidines with aryl carboxylic acids and aryl propargylic acids. The reactions occur at room temperature forming N-acylamidines which undergo tandem nucleophilic addition-deamination- intramolecular cyclisation to give the corresponding heterocyclic compounds in good to excellent yields. This one pot approach has led to the successful synthesis of the drug lead molecule, ataluren, 3-(5-(2-fluorophenyl)-1,2,4- oxadiazol-3-yl) benzoic acid in two steps. the Partner Organisations 2014.
Hydroxide-initiated conversion of aromatic nitriles to imidazolines: Fullerenes vs TCNE
Hou, Hui-Lei,Li, Zong-Jun,Li, Shu-Hui,Chen, Si,Gao, Xiang
supporting information, p. 4646 - 4649 (2013/10/08)
Transformation of aromatic nitriles to imidazolines has been achieved under basic conditions with the electron-deficient C60 and C70 fullerenes, but not with the electron-deficient olefin of tetracyanoethylene (TCNE). In situ UV-vis-
Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones
Zhang, Feng-Lian,Wang, Yi-Feng,Chiba, Shunsuke
, p. 6003 - 6007 (2013/09/12)
Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes
Photoinduced molecular rearrangements. The photochemistry of 1,2,4-oxadiazoles in the presence of sulphur nucleophiles. Synthesis of 1,2,4-thiadiazoles
Vivona, Nicolo,Buscemi, Silvestre,Asta, Stefano,Caronna, Tullio
, p. 12629 - 12636 (2007/10/03)
The photochemistry of some 1,2,4-oxadiazoles in the presence of sulphur nucleophiles has been investigated. Irradiation of the 5-amino-3-phenyl- and 3,5-diphenyl-1,2,4-oxadiazole at λ = 254 nm in methanol in the presence of sodium hydrogen sulphide or thiols gave a photo-induced redox reaction at the ring O-N bond, leading to the corresponding N-substituted benzamidines. By contrast, irradiation of the 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioureas or thiocarbamates, essentially gave 3-phenyl-5-substituted 1,2,4-thiadiazoles, which presume an N-S bond formation between the ring-photolytic species and the sulphur nucleophile. In turn, irradiation of the same 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioamides again afforded the redox reaction; in addition, amounts of 3-phenyl-5-substituted-1,2,4-thiadiazoles were also formed. Some mechanistic considerations are reported and synthetic methodologies leading to 1,2,4-thiadiazoles are emphasized.
REACTION OF NITRILES WITH 100percent SULFURIC ACID. INFLUENCE OF THE STRUCTURAL EFFECTS OF NITRILES ON THE DIRECTION OF TRANSFORMATION, THE CHARACTER OF COMPLEX FORMATION, AND THE FORM OF THE KINETIC EQUATION
Bodrikov, I. V.,Michurin, A. N.,Vasyanina, G. I.,Bochkareva, N. N.,Krasnoj, V. L.
, p. 2123 - 2133 (2007/10/02)
The competing directions and kinetics were studied for the reactions of nitriles with 100percent sulfuric aicd.The donor-acceptor interaction between the nitriles and sulfuric acid and DMSO was also investigated.It was shown that variation in the structural effects of the nitriles gives rise to change in the form of the kinetic equation, the ratio between the competing reaction paths, and the character of the donor-acceptor interaction.Situations where the nitrile does not enter into the kinetic equation of the reaction are the most typical.Methods for directed control of the ratio between the competing paths are given.The probable schemes for the mechanism of the reactions are discussed.
