Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides
Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides
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DOI：
10.1021/jo061043m
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发表时间：
2006-08-18
影响因子：
3.6
通讯作者：
Pelkey, Erin T.
中科院分区：
文献类型：
--
作者：
Coffin, Aaron R.;Roussell, Michael A.;Pelkey, Erin T.
以无环化合物为起始原料，经两步区域控制合成了3，4-二取代吡咯-2-甲醛。N-甲氧基-N-甲基-2-异氰乙酰胺与R-硝基烯烃或R-硝基乙酸酯进行Barton-Zard吡咯合成，得到N-甲氧基-N-甲基吡咯-2-甲酰胺（吡咯Weinreb酰胺），再用氢化铝锂处理，得到相应的吡咯-2-甲醛。吡咯-2-甲醛的区域选择性氧化得到相应的3，4-二取代的3-吡咯啉-2-酮。
A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and R-nitroalkenes or,-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides ( pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.