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Synthesis of 2-arylamino-3-cyanoquinolines via a cascade reaction through a nitrilium intermediate.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-01-14 , DOI: 10.1039/c9ob02427a Mani Ramanathan,Jing Wan,Yi-Hung Liu,Shie-Ming Peng,Shiuh-Tzung Liu
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-01-14 , DOI: 10.1039/c9ob02427a Mani Ramanathan,Jing Wan,Yi-Hung Liu,Shie-Ming Peng,Shiuh-Tzung Liu
A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of aryldiazonium salts and malononitrile, which undergoes intermolecular amination, Knoevenagel condensation, and then aromatization to yield the desired compound in moderate to good yields. This methodology features a quick assembly of C2 and C3 functionalized quinolines.
中文翻译:
通过腈中间体的级联反应合成2-芳基氨基-3-氰基喹啉。
报道了一种通过级联反应从易得的芳基重氮盐,2-氨基芳基酮和丙二腈制备2-氨基-3-氰基喹啉的新方法。这种一锅法涉及从芳基重氮盐和丙二腈的直接反应中原位生成N-芳基腈中间体,该中间体进行分子间胺化,Knoevenagel缩合,然后进行芳构化以中度到良好的收率得到所需化合物。该方法具有快速组装C2和C3功能化喹啉的特点。
更新日期:2020-02-13
中文翻译:
通过腈中间体的级联反应合成2-芳基氨基-3-氰基喹啉。
报道了一种通过级联反应从易得的芳基重氮盐,2-氨基芳基酮和丙二腈制备2-氨基-3-氰基喹啉的新方法。这种一锅法涉及从芳基重氮盐和丙二腈的直接反应中原位生成N-芳基腈中间体,该中间体进行分子间胺化,Knoevenagel缩合,然后进行芳构化以中度到良好的收率得到所需化合物。该方法具有快速组装C2和C3功能化喹啉的特点。