二氯二氰基苯醌在机械化学碳氮偶联反应中的应用
DDQ in mechanochemical C-N coupling reactions.
作者信息
Bera Shyamal Kanti, Bhanja Rosalin, Mal Prasenjit
机构信息
School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India.
出版信息
Beilstein J Org Chem. 2022 Jun 1;18:639-646. doi: 10.3762/bjoc.18.64. eCollection 2022.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3)-ones via the intra- and intermolecular C-N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp)-H amidation of -(2-(arylideneamino)phenyl)--toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3)-one derivatives in high yields.
2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）是一种广为人知的氧化剂。在此，我们报道DDQ可用于在无溶剂机械化学（球磨）条件下通过分子内和分子间C-N偶联反应合成1,2-二取代苯并咪唑和喹唑啉-4(3)-酮。在DDQ存在下，-(2-(亚芳基氨基)苯基)-对甲苯磺酰胺的分子内C(sp)-H酰胺化反应生成1,2-二取代苯并咪唑，2-氨基苯甲酰胺与芳基/烷基醛的一锅法偶联反应则以高产率得到取代的喹唑啉-4(3)-酮衍生物。
Zotero 插件