Affiliation:
1. Ural Federal University 19, Mira Street Yekaterinburg 620002 Russian Federation
2. Postovsky Institute of Organic Synthesis UB RAS 22/20, S. Kovalevskoy/Akademicheskaya Street Yekaterinburg 620990 Russian Federation
Abstract
AbstractA solvent‐free reaction between C6‐unsubstituted 5‐aryl‐1,2,4‐triazines and 2‐amino‐4‐aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza‐Diels‐Alder reaction between the oxazole moiety as dienophile and the 1,2,4‐triazine moiety as diene with the highly regioselective formation of 3,6‐diarylpyridines in up to 60 % isolated yield. The structure of one of the key‐products was proven by the X‐ray diffraction analysis, and the mechanism of the transformation was proposed. The reaction proceeds well for both 6‐aryl and 6‐hetaryl‐1,2,4‐triazines in the presence of the electron acceptor substituent at the position 3. In the case of the donor substituent in position 3, the pyridine yields are significantly reduced. In the case of 5,6‐nonsubstituted 1,2,4‐triazines, the triazine cycle is degraded without product formation. The high regioselectivity of the reaction as well as solvent‐free conditions are valuable advantages of the present synthetic approach.
Funder
Ministry of Science and Higher Education of the Russian Federation
Cited by
1 articles.
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