Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides.
The one-pot three-component reaction of secondary α-amino acids, including proline, thiazolidine-4-carboxylic acid, and piperidine-2-carboxylic acid sarcosine with dialkyl acetylenedicarboxylate and N-substituted maleimides in refluxing ethanol afforded functionalized pyrrolo[3,4-a]pyrrolizines, pyrrolo[3',4':3,4]pyrrolo[1,2-c]thiazoles, pyrrolo[3,4-a]indolizines and octahydropyrrolo[3,4-c]pyrroles in good yields and with high diastereoselectivity. On the other hand, the similar three-component reaction containing primary α-amino acids, such as glycine, alanine, phenylalanine and leucine, with N-substituted maleimides and two molecules of dialkyl acetylenedicarboxylate obtained the corresponding hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)maleates.
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China. sunjing@yzu.edu.cn cgyan@yzu.edu.cn.
Liang
L
Chen
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China. sunjing@yzu.edu.cn cgyan@yzu.edu.cn.
Jing
J
Sun
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China. sunjing@yzu.edu.cn cgyan@yzu.edu.cn.
Ju
J
Xie
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China. sunjing@yzu.edu.cn cgyan@yzu.edu.cn.
Chao-Guo
CG
Yan
D000114:Acetylene / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*
D000596:Amino Acids; D002264:Carboxylic Acids; D008301:Maleimides; D009584:Nitrogen; D000114:Acetylene