2,3‐Diodocarbazoles by a Domino Iodocyclization/Iodo‐Translocation of (3‐Iodoindolyl)butynols

A general electrophilic iodocyclization/nucleophile addition cascade transformation for 1,2-alkynediones for the synthesis of various oxygen heterocycles and access to regioselective alkyne hydroxylation is reported. Furan-tethered ynediones resulted in the construction of exo-enol ethers via carbonyl-alkyne cyclization-initiated heteroarene dearomatization, whereas other (hetero)arene-, alkenyl-, and alkyl-tethered ynediones resulted in the formation of highly functionalized 3(2H)-furanones. Importantly, the developed domino protocols involve the construction of important heterocyclic scaffolds and installation of two functional groups in a single operation. Moreover, the use of water as a nucleophile resulted in regioselective alkyne hydroxylation via furanone ring opening. The developed protocols are characterized by a wide substrate scope, and their utility has been demonstrated by a number of postsynthetic transformations.

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Iodocycloisomerization/Nucleophile Addition Cascade Transformations of 1,2-Alkynediones

Bag

Kour

Saha

et al. 2023

J. Org. Chem.

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2,3‐Diodocarbazoles by a Domino Iodocyclization/Iodo‐Translocation of (3‐Iodoindolyl)butynols

Abstract: A controlled access to 1‐aryl 2,3‐diiodo‐carbazoles involving iodine transposition has been accomplished directly from acyclic precursors. The 2,3‐diiodo‐carbazole core was prone to further chemoselective decoration at C3−I or double difunctionalization.

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Iodocycloisomerization/Nucleophile Addition Cascade Transformations of 1,2-Alkynediones

Iodocycloisomerization/Nucleophile Addition Cascade Transformations of 1,2-Alkynediones

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