α-Cyclization of tertiary amines. Part 2. Via (2 + 2) cycloaddition of β-aminoacrylonitriles with acetylenedicarboxylate

✍ Scribed by Shuiping Jiang; Zdenek Janousek; Heinz G. Viehe

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 181 KB
• Volume: 102
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19931021007

✦ Synopsis

The reaction of g-tert.aminoacrylonitriles 1 a-1 c with dimethyl acetylenedicarboxylate (DMAD) to give pyrrolizidine, indolizidine and pyrroloazepine is described. I n t r o d u c t i o n . T h e t h e r m a l " a -C y c l i z a t i o n o f T e r t i a r y A m i n e s " t o p y r r o l i d i n e , p y r r o l i z i d i n e , i n d o l i z i d i n e o r t o t h e i r h o m o l o g u e s 2 s u c c e e d s w e l l w i t h e l e c t r o n p o o r t e r t i a r y a m i n o d i e n e s 1 ( S c h e m e 1 ) .