Metal free C-H functionalization of diazines and related heteroarenes with organoboron species and its application in the synthesis of a CDK inhibitor, meriolin 1
Here, we report a metal-free cross-coupling reaction of diazines and related heteroarenes with organoboron species via C-H functionalization. The optimized conditions represent a metal-free method for the activation of aryl/heteroarylboronic acids, which undergo coupling with diazines and related heteroarenes. Optimized conditions also find application in the synthesis of a pyrimidine-based potent CDK inhibitor, meriolin1.
Thatikonda, Thanusha,Singh, Umed,Ambala, Srinivas,Vishwakarma, Ram A.,Singh, Parvinder Pal
p. 4312 - 4320
(2016/05/24)
Studies on Pyrimidine Derivatives. XXXIX. Site-Selectivity in the Reaction of 5-Substituted and 4,5-Disubstituted Pyrimidine N-Oxides with Trimethylsilyl Cynanide
The site-selectivity in the modified Reissert-Henze reaction of 5-substituted and 4,5-disubstituted pyrimidine 1-oxides with trimethylsilyl cyanide was examined.The reaction of 5-substituted 4-methoxypyrimidine 1-oxides with trimethylsilyl cyanide gave exclusively 2-pyrimidinecarbonitriles in good yields without exception.On the other hand, the other 5-substituted and 4,5-disubstituted pyrimidine 1-oxides gave mainly 6-pyrimidinecarbonitriles.Keywords--site-selectivity; pyrimidine N-oxide; trimethylsilyl cyanide; Reissert-Henze reasction; pyrimidinecarbonitrile
INVESTIGATION OF SOME ELECTROPHILIC REACTIONS OF 4-PHENYL-5-HYDROXYPYRIMIDINE AND ITS 1-OXIDE
A difference in the reactivities of the 2 and 6 positions of the 5-hydroxypyrimidine ring and an effect of the N-oxide group on the direction of electrophilic substitution reactions were demonstrated in the case of synthesized 4-phenyl-5-hydroxypyrimidine and its 1-oxide.
Gashev, S. B.,Sedova, V. F.,Smirnov, L. D.,Mamaev, V. P.
p. 1008 - 1012
(2007/10/02)
Selective brominations in nitrobenzene. A convenient synthesis of 3 bromoquinoline, 4 bromoisoquinoline, and 4 phenyl 5 brompyrimidine
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Kress,Costantino
p. 409 - 410
(2007/10/04)
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