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

Autor: Dong X; Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China., Ma P; Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China., Zhang T; Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China., Jalani HB; Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City 758307, Vietnam.; Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City 758307, Vietnam., Li G; Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States., Lu H; Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2020 Oct 16; Vol. 85 (20), pp. 13096-13107. Date of Electronic Publication: 2020 Oct 02.
DOI: 10.1021/acs.joc.0c01789
Abstrakt: 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 -NH 2 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.
Databáze: MEDLINE