通过 Cadogen 型反应串联合成吡咯并[2,3-b]喹啉
Tandem Synthesis of Pyrrolo[2,3-b]quinolones via Cadogen-Type Reaction.
机构信息
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University , Jinan 250014, China.
出版信息
Org Lett. 2017 Oct 6;19(19):5284-5287. doi: 10.1021/acs.orglett.7b02558. Epub 2017 Sep 14.
A tandem [3 + 2] cycloaddition/reductive cyclization of nitrochalcones with activated methylene isocyanides for the efficient synthesis of pyrrolo[2,3-b]quinolones is reported. In this reaction, the in situ generated dihydropyrroline acts as the internal reductant to convert the nitro into an electrophilic nitroso group, which undergoes subsequent C-N bond formation. Transition-metal-free, simple experimental procedure and ready accessibility of starting materials characterize the present transformation.
硝基查耳酮与活性亚甲基异氰化物的串联[3 + 2]环加成/还原环化反应高效合成了吡咯并[2,3-b]喹啉酮。在该反应中，原位生成的二氢吡咯啉充当内部还原剂，将硝基转化为亲电的亚硝基，随后进行 C-N 键形成。该转化具有无过渡金属、实验步骤简单以及起始原料易得的特点。
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