Reactivity of functionalized N,S-ketene acetal: regioselective construction of tetrahydrobenzo[b]pyran and chromeno[2,3-b]quinoline derivatives.
Reactivity of functionalized N,S-ketene acetal: regioselective construction of tetrahydrobenzo[b]pyran and chromeno[2,3-b]quinoline derivatives.
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DOI：
10.1021/jo101902z
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发表时间：
2010-11
期刊：
影响因子：
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通讯作者：
Ming Li;Yan-Li Hou;L. Wen;Fu‐Meng Gong
中科院分区：
文献类型：
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作者：
Ming Li;Yan-Li Hou;L. Wen;Fu‐Meng Gong
以β-苯甲酰基硫代乙酰苯胺或β-（2-卤代芳酰基）硫代乙酰苯胺为原料，在三乙胺催化下，分别与芳香醛和5，5-二甲基-1，3-环己二酮进行多组分反应（MCR）和串联[3 + 3]环化反应，区域选择性地合成了功能化的四氢苯并[B]吡喃。在此MCR之后，在K（2）CO（3）的存在下，通过分子内S（N）Ar进行后缩合环化，以良好的产率产生了前所未有的含有重要的色烯部分的新型色烯并[2，3-B]喹啉骨架。该反应非常温和，方便，并且具有O-选择性，可形成新的稠合四环目标分子。
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.