کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5275051 | 1385524 | 2009 | 4 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams](/preview/png/5275051.png)
An effective route to novel polysubstituted imides is described, which involves the reaction of enaminonitrile γ-lactams derived from N-alkylated α-bromoacetamides and malononitrile with acryloyl chloride derivatives. This preceded via a sequence 1,4-addition-intramolecular peptidic coupling and a γ-lactam hydrolysis in a one 'pot-procedure'. These imides were regioselectively reduced into corresponding N-acyliminium precursors, which subsequently submitted to an intramolecular aza-cyclization in acidic medium to provide novel 7-hexahydro-aza-indoles.
The scope of reactions of enaminonitrile γ-lactams, obtained easily from N-alkylated α-bromoacetamides and malononitrile, with acryloyl chloride derivatives has been extended successfully in forming novel polysubstituted imides. From these results, the tandem ring closure/ring opening seems to be effective and general. The latter systems obtained were then used to provide substituted 7-hexahydro-aza-indoles by using a regioselective reduction process followed ultimately by aza-cationic cyclization in acidic medium.
Journal: Tetrahedron Letters - Volume 50, Issue 13, 1 April 2009, Pages 1459-1462