Organocatalyzed Modular Synthesis of Polycyclic Dihydropyridines and Pyridines through Sulfamate Linchpin

Bhajammanavar, Vinod; Sureshbabu, Popuri; Reddy, Mallu Kesava; Baidya, Mahiuddin

doi:10.1002/asia.202200400

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2023

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Cited by 3 publications

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Swapping Copper‐Catalytic Process: Selective Access to Pyrazoles and Conjugated Ketimines from Oxime Acetates and Cyclic Sulfamidate Imines

Prakash

Halder

Guin

et al. 2023

Chemistry An Asian Journal

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A powerful CuCl-catalyzed sequential one-pot reaction of aryl methyl ketoxime acetates with cyclic Nsulfonyl imines followed by elimination in the presence of base is reported. This hydrazine-free method conveniently makes CÀ C and NÀ N bonds via a radical cleavage of the NÀ O bond, delivering a special class of C3-hydroxyarylated pyrazoles in good yields. Surprisingly, while employing CuI as a catalyst instead of CuCl, the reaction proceeds through a non-radical pathway which embodies a new tactic for the high-yielding access to value-added conjugated N-unsubstituted ketimines. Moreover, additive-free approach to sulfamidate-fused-pyrazoles was achieved by successfully catalyzing addition and oxidative NÀ N bond-making reactions by CuI and CuCl, respectively. Significantly, our novel technique could convert the prepared ketimines into the pharmacologically recognized 6H-benzo[c]chromene frameworks.

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