4.5 Review

The Synthetic Progress of Fused Bicyclic N,O-acetals

Journal

CURRENT ORGANIC CHEMISTRY
Volume 26, Issue 24, Pages 2203-2213

Publisher

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1385272827666230217090408

Keywords

N; O-acetals; hetero-Diels-Alder (hetero-DA); multicomponent domino reaction (MCR); hydroxyl groups; cyclic enamines; cycloaddition

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This mini-review provides a summary of the synthetic progress of fused bicyclic N,O-acetals. Different reaction types, including hetero-Diels-Alder cycloaddition, step-by-step reactions, [3+2] cycloaddition, and other novel strategies, are elaborated. The catalytic systems and reaction mechanisms are also described in detail.
Owing to the prevalent occurring in natural products and abundant bioactivities, the effective synthetic methods of fused bicyclic N,O-acetals skeletons are of great interest to chemists. This mini-review summarized the thus far synthetic progress of fused bicyclic N,O-acetals. These works were elaborated according to the different reaction types, including a) hetero-Diels-Alder cycloaddition of cyclic enamines with oxadienes; b) step-by-step reactions between cyclic enamines and electrophiles with pendant hydroxyl groups; c) [3+2] cycloaddition of indole with quinone or its equivalent and d) other novel strategies. The catalytic systems and reaction mechanisms are mainly described.

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