One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles
One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles
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DOI：
10.1021/ja803139k
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发表时间：
2008-07-09
影响因子：
15
通讯作者：
Davies, Huw M. L.
中科院分区：
文献类型：
--
作者：
Manning, James R.;Davies, Huw M. L.
开发了一种高度官能化吡啶的简明一锅法合成方法。反应顺序的第一步是在异恶唑的 N-O 键上正式插入铑乙烯基类胡萝卜素。加热后，插入产物发生重排，生成 1,4-氢吡啶。然后DDQ氧化得到相应的吡啶，产率为31-84%。该工艺已被证明适用于一系列类胡萝卜素和异恶唑组分，并且代表了合成官能化吡啶的独特断开策略。
A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-hydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general with a range of carbenoid and isoxazole components and represents a unique disconnection strategy for the synthesis of functionalized pyridines.