2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines
Alexey P. Krinochkin, Guda Mallikarjuna Reddy, Dmitry S. Kopchuk, Павел А. Слепухин, Ya. K. Shtaitz, Igor А. Khalymbadzha, Igor S. Коvalev, Grigory А. Кim, I.N. Ganebnykh, Grigory V. Zyryanov, Олег Н. Чупахин, Valery N. Charushin
Abstract
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.
Topics & Concepts
ChemistryMoietyOxazoleDieneDiels–Alder reactionStereochemistryMedicinal chemistryOrganic chemistryCatalysisNatural rubberSynthesis and Characterization of Heterocyclic CompoundsChemical Reaction MechanismsSynthesis and Biological Evaluation