31409-38-8Relevant academic research and scientific papers
A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes: Via the [3 + 2]-dipolar cycloaddition of imidazole N -oxides and 2-heteroaryl-3,3-dimethylacrylonitriles
Kutasevich, Anton V.,Niktarov, Anton S.,Uvarova, Ekaterina S.,Karnoukhova, Valentina A.,Mityanov, Vitaly S.
, p. 8988 - 8998 (2021/11/09)
A new synthetic approach for obtaining previously unknown bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes has been developed. It is based on 1,3-dipolar cycloaddition between 2-unsubstituted imidazole N-oxides and 2-(1,3-azol-2-yl)-3,3-dimethylacrylonitriles, which are easily available through the condensation of (1,3-azol-2-yl)acetonitriles with acetone. The method allows for the construction of various unsymmetric derivatives based on imidazole, oxazole, thiazole, and 1,3,4-thiadiazole cyclic molecules. Its potential has been demonstrated via the synthesis of 24 diverse derivatives with yields of 29-92%. Bis(1,3-azol-2-yl)acetonitriles can be converted to the corresponding bis(1,3-azol-2-yl)methanes via simple acid hydrolysis followed by subsequent spontaneous decarboxylation at nearly quantitative yields.
Unexpected Aldehyde-Catalyzed Reaction of Imidazole N -Oxides with Ethyl Cyanoacetate
Efimova, Anna S.,Kutasevich, Anton V.,Kuz'Mina, Ludmila G.,Mityanov, Vitaly S.,Perevalov, Valery P.,Sizonenko, Marina N.
, p. 179 - 182 (2020/01/23)
The reaction of 2-unsubstituted imidazole N -oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2 H -imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.
Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3- oxides
Mloston, Grzegorz,Celeda, Malgorzata,Prakash, G. K. Surya,Olah, George A.,Heimgartner, Heinz
, p. 728 - 138 (2007/10/03)
The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5°leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N- acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me3SiCN) in CH2Cl2 at 0-5°(Scheme 3).
