Bharadwaj Ashwin R, Scheidt Karl A
Northwestern University, Department of Chemistry, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
Org Lett. 2004 Jul 8;6(14):2465-8. doi: 10.1021/ol049044t.
[reaction: see text] A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.
[反应:见正文] 已公开了一种由噻唑鎓盐催化的多组分合成高度取代吡咯的方法。该反应采用酰基硅烷(硅-Stetter反应)与不饱和酮的酰基阴离子共轭加成反应原位生成1,4-二羰基化合物。随后加入各种胺促进Paal-Knorr反应,通过高效的一锅法得到所需的吡咯核。