Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of L-α-aminoacids
Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of L-α-aminoacids
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DOI：
10.1016/j.tetlet.2009.01.074
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发表时间：
2009-04-01
影响因子：
1.8
通讯作者：
Zecchi, Gaetano
中科院分区：
文献类型：
--
作者：
Broggini, Gianluigi;Galli, Simona;Zecchi, Gaetano
Boc-保护的α-氨基酸的丙二烯基酰胺在碱性介质中容易产生杂环产物，该杂环产物由NH基团攻击1，2-二烯部分的内侧C-C双键产生，即咪唑烷酮、吡嗪酮和吡咯化合物。微波辅助的杂环化干净地发生在丙二烯基的C-β处，形成具有环内或环外双键的吡嗪-2-酮。(C)2009爱思唯尔有限公司版权所有。
Allenylamides of Boc-protected alpha-aminoacids easily gave in basic medium heterocyclic products arising from attack of the NH group on the inside C-C double bond of the 1,2-diene moiety, namely imidazolidinones, pyrazinones, and a pyrrole compound. The microwave-assisted heterocyclization occurred cleanly at C-beta of the allenyl group with formation of pyrazin-2-ones having an endo- or exocyclic double bond. (C) 2009 Elsevier Ltd. All rights reserved.