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J Org Chem. 2015 Jun 5;80(11):5764-70. doi: 10.1021/acs.joc.5b00727. Epub 2015 May 8.

Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization.

Author information

1
†School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
2
§Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States.

Abstract

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.

PMID:
25919002
DOI:
10.1021/acs.joc.5b00727
[Indexed for MEDLINE]

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