State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 53 Zhengzhou Road, Qingdao 266042, PR China.
J Org Chem. 2010 Dec 17;75(24):8522-32. doi: 10.1021/jo101902z. Epub 2010 Nov 18.
Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multicomponent reactions (MCRs) and tandem [3 + 3] annulations of β-benzoylthioacetanilides or β-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular S(N)Ar in the presence of K(2)CO(3) led to an unprecedented novel chromeno[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.
通过多组分反应（MCRs）和β-苯甲酰硫代乙酰胺或β-（2-卤代甲酰基）硫代乙酰胺与芳香醛和 5,5-二甲基-1,3-环己二酮的串联[3+3]环加成，开发了功能化四氢苯并[b]吡喃的区域选择性合成。三乙胺催化下，该 MCR 随后在 K2CO3存在下通过分子内 S（N）Ar 进行后缩合环化，得到了一种前所未有的新型色烯并[2,3-b]喹啉骨架，其中含有重要的色烯部分，产率良好。反应条件非常温和、方便，且对形成新的稠合四环目标分子具有 o-选择性。
