Fused Tetracyclic Heterocycles by Thermally Initiated Intramolecular Criss-Cross Cycloaddition of 3-Substituted Homoallenylaldazines
作者:Hana Zachová、Stanislav Man、Marek Nečas、Milan Potáček
DOI:10.1002/ejoc.200400814
日期:2005.6
A thermally initiated intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines (5) was searched. Their cyclization led to interesting new fused heterocyclic systems consisting of four five-membered rings with two nitrogen heteroatoms (6). The preparation of azines was based on application of homoallenylaldehydes (4) in reaction with hydrazine. The homoallenylaldehydes
研究了热引发的 3-取代对称高烯基吖嗪 (5) 的分子内交叉环加成反应。它们的环化导致了有趣的新稠合杂环系统,该系统由四个五元环和两个氮杂原子组成 (6)。吖嗪的制备基于高烯基醛 (4) 与肼反应的应用。高烯醛 (4) 通过新的 N,N-二取代 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-胺 (3a-f) 的克莱森重排制备由 2-methylprop-1-en-1-yl prop-2-yn-1-yl 醚 (2) 通过曼尼希反应制备。该反应的成功基于改进的 1-氯-2-甲基丙基丙-2-炔-1-基醚 (1) 合成的无溶剂程序及其转化为完全可分离的 2-甲基丙-1-烯-1-基高产率的丙-2-炔-1-基醚(2)。