Cyclization of 5,6-Diarylpyrrolo[3,4-d]pyrimidine-2,4-diones into Pyrrolo[1,2-f]phenanthridine Derivatives: Intramolecular C–H Arylation under Ru/NHC Catalysis

• Published in: Russian journal of general chemistry Vol. 94; no. 2; pp. 327 - 336
• Main Authors: Tkachenko, Yu. N., Shevchenko, M. A., Lavrentev, I. V., Pasyukov, D. V., Minyaev, M. E., Chernyshev, V. M.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-02-2024; Springer Nature B.V
• Subjects: Catalysis; Catalytic activity; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Diketones; Imidazole; Pyrimidines; ruthenium; Ru/NHC; catalysis; intramolecular C–H arylation; pyrrolopyrimidine; pyrrolophenathridine
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363224020087

The cyclization of 5,6-diarylpyrrolo[3,4-
d
]pyrimidine-2,4-diones containing a halogen atom in the
ortho
-position of one of the aryl rings, proceeding as intramolecular C–H arylation catalyzed by Ru(II) complexes, was studied. It was found that complexes Ru(NHC)(cymene)Cl
2
, where NHC = IPr [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], IMes [1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene], and their derivatives containing substituents at positions 4 and 5 of the imidazole ring, exhibit high catalytic activity. Based on the reaction studied, new representatives of pyrimido[5',4':3,4]pyrrolo[1,2-
f
]phenanthridine were obtained.