Trifluoroethanol Promoted Castagnoli-Cushman Cycloadditions of Imines with Homophthalic Anhydride.

ABSTRACT: Lactams are essential compounds in medicinal chemistry and key intermediates in the synthesis of natural products. The Castagnoli-Cushman reaction (CCR) of homophthalic anhydride with imines is an exciting method for accessing cyclic densely substituted lactam products. Most CCRs need to be catalyzed or heated. Herein, we report a new, efficient, metal and catalyst-free CCR for the synthesis of poly-substituted 3,4-lactams utilizing the unique properties of trifluoroethanol (TFE). This procedure provides high-speed and smooth access to a broad range of densely substituted 3,4-lactams in good yields and a 100% atom-economical fashion.

SUBMITTER: Bayles T 

PROVIDER: S-EPMC8839191 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature