A. P. Krinochkin, G. M. Reddy, D. S. Kopchuk, P. A. Slepukhin, Ya. K. Shtaitz, I. A. Khalymbadzha, I. S. Kovalev, G. A. Kim, I. N. Ganebnykh, G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin, “2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines”, Mendeleev Commun., 2021, том 31, выпуск 4,страницы 542

Эта публикация цитируется в 25 статьях

2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines

A. P. Krinochkin^ab, G. M. Reddy^b, D. S. Kopchuk^ab, P. A. Slepukhin^ab, Ya. K. Shtaitz^b, I. A. Khalymbadzha^ab, I. S. Kovalev^b, G. A. Kim^ab, I. N. Ganebnykh^a, G. V. Zyryanov^ab, O. N. Chupakhin^ab, V. N. Charushin^ab

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation

Аннотация: High temperature coupling of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.

Ключевые слова: 1,2,4-triazines, oxazol-2-amines, inverse electron demand reactions, Diels–Alder reaction, 2,2'-bipyridin-3-ols, solvent-free reactions.

Язык публикации: английский

DOI: 10.1016/j.mencom.2021.07.035