A 10 A catalyst and additive-free three-component reaction of highly electrophilic azides with cyclic ketones and cycloaliphatic amines. Synthesis of novel N-heteroaryl amidines [Electronic resource] / I. Efimov, N. Beliaev, T. Beryozkina, P. A. Slepukhin, V. A. Bakulev // Tetrahedron Letters. - 2016. - Vol. 57, № 18. - С. 1949-1952 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SULFONYL AMIDINES; -- KETENE N,X-ACETALS -- CYCLOADDITION REACTIONS Аннотация: Highly electrophilic 5-azido-1-methyl-4-nitro-1H-imidazole and sulfonyl azides were demonstrated to react with alicyclic amines and cyclic ketones in the absence of any catalyst or additive to afford novel N-(4-nitroimidazol-5-yl)- or N-sulfonylamidines respectively. Based on single crystal X-ray analysis, a revision of the previously reported data of Gao and co-workers on the direction of the reaction of sulfonyl azides with endocyclic enamines was made. The reaction of 2,6-diazidopyridine with an enamine, 4-(cyclohex-1-en-l-yl)morpholine, proceeded with cyclization of the azide moiety onto the pyridine C=N bond to form an amidine bearing the tetrazolo[1,5-a]pyridine fragment. \\\\expert2\\NBO\\Tetrahedron Letters\\2016, v. 57, p. 1949.pdf |