Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: Convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives
Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: Convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives
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DOI：
10.1021/jo062626z
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发表时间：
2007-03-16
影响因子：
3.6
通讯作者：
Riva, Renata
中科院分区：
文献类型：
--
作者：
Banfi, Luca;Basso, Andrea;Riva, Renata
研究了一种基于Ugi多组分反应和随后的分子内S（N）2反应的合成二氮杂环庚烷或二氮杂环辛烷体系的两步法。1-通过Ugi多组分反应和Mitsunobu环合反应，以很高的收率得到磺酰基四氢苯并[e]-1，4-二氮杂卓-1-酮1。另一方面，脂肪族1-磺酰基1，4-二氮杂环庚烷-5-酮2可以采用不同的环化条件（磺酰基二咪唑）得到。使用异羟肟酸酯作为亲核试剂的类似方法对重氮杂环辛烷环不太成功，仅提供O-环化加合物或意想不到的副产物。提出了一个机制的解释所观察到的结果。
A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.