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Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles.

ABSTRACT: We report herein a copper-catalyzed sequential multicomponent reaction of benzo[d]isoxazoles with terminal alkynes and sulfonyl azides, which produced divergent 4-amino-2H-chromen-2-imines with excellent chemical selectivity. The reaction tolerated a broad range of functional groups, and released only N2 as the sole byproduct. The sulfonyl imino group could be removed to give biologically active free 4-amino-2H-chromenone in good yield.

SUBMITTER: Chen Z

PROVIDER: S-EPMC6644361 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles.

Chen Zhiyuan Z Han Cuifen C Fan Congbin C Liu Gang G Pu Shouzhi S

ACS omega 20180723 7

We report herein a copper-catalyzed sequential multicomponent reaction of benzo[d]isoxazoles with terminal alkynes and sulfonyl azides, which produced divergent 4-amino-2H-chromen-2-imines with excellent chemical selectivity. The reaction tolerated a broad range of functional groups, and released only N2 as the sole byproduct. The sulfonyl imino group could be removed to give biologically active free 4-amino-2H-chromenone in good yield. ...[more]

PMID: 31458953

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