Synthesis of a New Heterocyclic System: Pyrimidine Structural Analogues of Natural Integrastatins A, B
Chikunov S.Y. Pustolaikina I.A. Gatilov Y.V. Kulakov I.V.
3 September 2024Georg Thieme Verlag
Synlett
2024#35Issue 151799 - 1806 pp.
In this paper for the first time, we report a simple one-step synthesis of 5-methyl-11,12-dihydro-5 H -5,11-epoxybenzo[7,8]oxocino[4,3- d ]pyrimidine derivatives by acid-catalyzed cyclization reaction of various 4-methyl-5-acetyl pyrimidine derivatives with salicylic aldehyde. It was shown that 2-substituted 4-methyl-5-acetylpyrimidines successfully react to form a cyclization product. At the same time, 4-methyl-5-acetylpyrimidines with a substituent in the 6 th position do not enter into the cyclization reaction. This may be caused by the negative effect of substituents in the 6 th position, which hinder the free rotation of the acetyl group and prevent the formation of a stable pre-reaction complex. The structures of the obtained 5-methyl-11,12-dihydro-5 H -5,11-epoxybenzo[7,8]oxocino[4,3- d ]pyrimidine derivatives were confirmed using 1 H NMR and 13 C NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis.
4-methyl-5-acetyl derivatives of pyrimidine , epoxybenzo[7,8]oxocino[4,3- d ]pyrimidines , integrastatins , intramolecular cyclization , salicylic aldehyde
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Institute of Chemistry, Tyumen State University, 15a Perekopskaya St., Tyumen, 625003, Russian Federation
Laboratory of Theory and Optimization of Chemical and Technological Processes, Tyumen State University, 15a Perekopskaya St., Tyumen, 625003, Russian Federation
Karagandy University of the name of academician E.A. Buketov, Karaganda, 100024, Kazakhstan
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Science, 9 Akademika Lavrientieva Ave., Novosibirsk, 630090, Russian Federation
Institute of Chemistry
Laboratory of Theory and Optimization of Chemical and Technological Processes
Karagandy University of the name of academician E.A. Buketov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
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