Synthesis of Pyridopyrimidines by Palladium-Catalyzed Isocyanide Insertion
Synthesis of Pyridopyrimidines by Palladium-Catalyzed Isocyanide Insertion
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DOI：
10.1021/cs400926z
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发表时间：
2014-01-01
期刊：
影响因子：
12.9
通讯作者：
Ruijter, Eelco
中科院分区：
文献类型：
--
作者：
Estevez, Veronica;Van Baelen, Gitte;Ruijter, Eelco
报道了一种基于钯催化异氰化物与易得的N-溴代吡啶反应合成4-氨基吡啶-[2，3-d]嘧啶和4-氨基吡啶[3，2-d]嘧啶的新方法。目标杂环化合物的产率一般为好到极好。对于两个区域异构体的嘧啶类化合物，我们比较了我们的氧化加成方法和类似的C-H活化法，因为这两种方法都已被报道用于合成4-氨基喹唑啉。我们发现，C H活化方案不允许人们获得目标的吡啶并嘧啶类化合物，但亚胺化交叉偶联方案为合成这些具有重要医学意义的支架提供了一个新的途径。
A new synthetic approach to 4-aminopyrido-[2,3-d]pyrimidines and 4-aminopyrido[3,2-d]pyrimidines based on palladium-catalyzed reaction of isocyanides with readily available N-(bromopyridyl)amidines is reported. The target heterocycles were obtained in generally good to excellent yield. For the two regioisomeric pyrimidopyrimidines, we compared our approach involving oxidative addition with the analogous C H activation protocol because both methods have been reported for the synthesis of 4-aminoquinazolines. We found that the C H activation protocol does not allow one to obtain the target pyridopyrimidines, but the imidoylative cross-coupling protocol provided a new entry to the synthesis of these medicinally important scaffolds.