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Synthesis 1997; 1997(12): 1389-1390
DOI: 10.1055/s-1997-1367
DOI: 10.1055/s-1997-1367
short paper
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Studies on Isocyanides and Related Compounds. An Unusual Synthesis of Functionalized Succinimides
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synthesis/199712/lookinside/thumbnails/10.1055-s-1997-1367-1.jpg)
The treatment of (E)-2-[(N-chloroacetyl-N-(4-nitrophenyl)amino]-4-phenylbut-3-enoic acid N-cyclohexamide (6a) with KOH does not afford the expected β-lactam 1a but the succinimide 7a, probably through a ring enlargement of compound 1a itself. A hypothesis on the reaction mechanism, which is corroborated by experimental results, is formulated.
isocyanides - Ugi four-component condensation (4CC) - β-lactams - ring enlargement - succinimides