Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization.
A palladium-catalyzed isocyanide insertion-cyclization using low-cost and readily accessible 2-haloanilines, 2-iodophenylethanones, and isocyanides for efficient synthesis of 3-iminoindol-2-amine and cyclic enaminone derivatives has been developed. The method features low-cost and readily accessible starting materials, reliable scalability, and bond-forming efficiency as well as simple one-pot operation, which makes this strategy highly attractive. A reasonable mechanism for forming 3-iminoindol-2-amine involved double isocyanide insertion/cyclization process is proposed.
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Yuan-Yuan
YY
Pan
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Ya-Nan
YN
Wu
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Zhen-Zhen
ZZ
Chen
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Wen-Juan
WJ
Hao
§Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States.
Guigen
G
Li
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Shu-Jiang
SJ
Tu
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Bo
B
Jiang
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000588:Amines; D003486:Cyanides; D007211:Indoles; D010165:Palladium