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通过亚硝化反应和 2-芳基吲哚的铁(III)催化的顺序 C-C 键断裂合成 2-氨基苯甲腈。

Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles.

机构信息

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry and Pharmaceutical Sciences , Guangxi Normal University , 15 Yu Cai Road , Guilin , 541004 , China.

出版信息

Org Lett. 2018 Jun 15;20(12):3527-3530. doi: 10.1021/acs.orglett.8b01294. Epub 2018 May 25.

DOI:10.1021/acs.orglett.8b01294
PMID:29798675
Abstract

A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.

摘要

通过叔丁基亚硝酰(TBN)介导的亚硝化和一锅法中铁(III)催化的连续 C-C 键断裂,从 2-芳基吲哚中制备了各种 2-氨基苯甲腈,产率良好至优秀。2-氨基苯甲腈可通过分子内环化缩合迅速合成苯并恶嗪酮。本方法的特点是使用廉价的铁(III)催化剂、克级规模的制备和吲哚的新型 C-C 键断裂。

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