Allenic Compounds and Isothiocyanates as Key Building Units in the Synthesis of Heterocycles
Allenic Compounds and Isothiocyanates as Key Building Units in the Synthesis of Heterocycles
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DOI：
10.1002/chin.200427267
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发表时间：
2004-04
期刊：
影响因子：
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通讯作者：
L. Brandsma;N. Nedolya
中科院分区：
文献类型：
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作者：
L. Brandsma;N. Nedolya
锂化联烯化合物与异硫氰酸酯之间的反应，R 'N =C=S，在大多数情况下仅产生具有联烯结构的硫代亚氨酸酯，C=C=CC（SLi）=NR 1。这些中间体已用于制备2，3-二氢吡啶、吡咯、喹啉、环丁烷吡咯啉和噻吩或二氢噻吩衍生物的新方法中。产生在环中具有氮原子的杂环的程序包括5-烷基化，然后简单加热或用卤化铜（I）处理。2-氨基噻吩和2-亚氨基-2，5-二氢噻吩是通过硫醇基部分在丙二烯体系上的分子内亲核攻击和随后的碘甲烷加成或质子化而形成的。1引言2丙二烯锂化合物的产生3 2，3-二氢吡啶或2，3-二氢吡啶和吡咯的混合物的形成4吡咯的定向合成5喹啉的合成6环丁烷吡咯啉的合成7噻吩和二氢噻吩衍生物的合成8结束语。
Reaction between lithiated allenic compounds and isothiocyanates, R'N=C=S, in most cases gives exclusively thioimidates with the allenic structure, C=C=CC(SLi)=NR 1 . These intermediates have been used in novel approaches to 2,3-dihydropyridines, pyrroles, quinolines, cyclobutanopyrrolines, and thiophene or dihydrothiophene derivatives. The procedures leading to the heterocycles with a nitrogen atom in the ring involve 5-alkylation followed by simple heating or by treatment with copper(I) halide. 2-Aminothiophenes and 2-imino-2,5-dihydrothiophenes are formed by intramolecular nucleophilic attack of the thiolate moiety on the allenic system and subsequent addition of methyl iodide or protonation. 1 Introduction 2 Generation of Allenic Lithium Compounds 3 Formation of 2,3-Dihydropyridines or Mixtures of 2,3-Dihydropyridines and Pyrroles 4 Directed Synthesis of Pyrroles 5 Synthesis of Quinolines 6 Synthesis of Cyclobutanopyrrolines 7 Synthesis of Thiophene and Dihydrothiophene Derivatives 8 Concluding Remarks.