Iridium-Catalyzed C-H Amination of Weinreb Amides: A Facile Pathway toward Anilines and Quinazolin-2,4-diones

Xunqing Dong, Panpan Ma, Tao Zhang, Hitesh B. Jalani, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.

Original languageEnglish
Pages (from-to)13096-13107
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number20
DOIs
StatePublished - Oct 16 2020

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