多组分反应和串联反应.ppt

1、多组分反应 91, 349 (1854).,2020/7/26,12,2020/7/26,13,2020/7/26,14,SYNLETT 2007, No. 2, pp 0318032001.02.207,2020/7/26,15,Hantzsch 二氢吡啶合成,Synthesis of dihydropyridines by condensation of two moles of a -dicarbonyl compound with one mole of an aldehyde in the presence of ammonia. Dehydrogenation to the cor

2、responding pyridine is accomplished with an oxidizing agent,A. Hantzsch, Ann. 215, 1, 72 (1882); Ber. 18, 1744 (1885); 19, 289 (1886).,2020/7/26,16,2020/7/26,17,2020/7/26,18,Biginelli 二氢吡啶合成,Synthesis of tetrahydropyrimidinones by the acid-catalyzed condensation of an aldehyde, a -keto ester and ure

3、a,P. Biginelli, Ber. 24, 1317, 2962 (1891); 26, 447 (1893).,2020/7/26,19,2020/7/26,20,Aldehyde building blocks,2020/7/26,21,CH-Acidic carbonyl building blocks,2020/7/26,22,Urea-type building blocks,Combinatorial diversity in dihydropyrimidines,2020/7/26,23,2020/7/26,24,Passerini 反应,Formation of -hyd

4、roxycarboxamides on treatment of an isonitrile with a carboxylic acid and an aldehyde or ketone,M. Passerini, Gazz. Chim. Ital. 51, 126, 181 (1921).,2020/7/26,25,反应机理,2020/7/26,26,2020/7/26,27,2020/7/26,28,Ugi 反应,利用醛、胺、羧酸、异腈间的反应一步合成-酰胺基酰胺的反应。 Ugi反应（亚胺）与Passerini反应（醛）机理类似 绿色反应，唯一的副产物是水 过去10多年里研究最多的反应

5、之一,Ugi, Angew. Chem. Int. Ed. 1, 8 (1962).,2020/7/26,29,亚胺的生成、亚胺被酸质子化、亲电亚胺盐和亲核羧基阴离子对异腈的-加成、分子内的酰基转移,2020/7/26,30,2020/7/26,31,2020/7/26,32,异腈参与的类似新反应,1999,2020/7/26,33,Gewald 噻吩合成,Gewald, et al. Chem. Ber. 99, 94-100 (1966).,2020/7/26,34,2020/7/26,35,2020/7/26,36,2020/7/26,37,Pauson-Khand 反应,炔烃、一氧化碳

6、、烯烃在钴催化下形成环戊烯酮,2020/7/26,38,2020/7/26,39,Asinger反应,Asinger, Angew. 68, 377，413 (1956).,2020/7/26,40,4+2环加成,2020/7/26,41,3+2环加成,2020/7/26,42,七组分反应,2020/7/26,43,全合成应用,2020/7/26,44,参考书目,2020/7/26,45,串联反应,两步或更多步反应连续发生，不经中间产物的分离，直接得到最终产物的一连串反应 Tandem Reactions、Cascade Reactions、Domino Reactions, Sequential Reactions,2020/7/26,46,Baylis-Hillman Reaction,Michael-Aldol串联,2020/7/26,47,2020/7/26,48,Michael-Aldol串联,2020/7/26,49,Michael-Michael串联,Angew. Chem. Int. Ed. 2008, 47, 4177 4179,2020/7/26,50,Michael-Alkyaltion串联,2020/7/26,51,2020/7/26,52,Michael-Alkylation串联,2020/7/26,53,Michael-He