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Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N?3/C-Sulfonyl Migration.

ABSTRACT: A completely regioselective and highly stereoselective palladium-catalyzed intramolecular hydroarylation of arenesulfonyl ynamines to benzothiazoles was developed. The presence of an electron-withdrawing group on the triple bond of the sulfonyl ynamine was crucial for the success of the reaction and our mechanistic studies suggest an alkyne-directed 5-exo-dig cyclization pathway. The products easily underwent photoinduced rearrangement to 3-amino-1-benzothiophene-1,1-diones (up to 35?% yields after two steps).

SUBMITTER: Bernar I

PROVIDER: S-EPMC6220774 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration.

Bernar Ivan I Blanco-Ania Daniel D Stok Sophie J SJ Sotorríos Lia L Gómez-Bengoa Enrique E Rutjes Floris P J T FPJT

European journal of organic chemistry 20181010 39

A completely regioselective and highly stereoselective palladium-catalyzed intramolecular hydroarylation of arenesulfonyl ynamines to benzothiazoles was developed. The presence of an electron-withdrawing group on the triple bond of the sulfonyl ynamine was crucial for the success of the reaction and our mechanistic studies suggest an alkyne-directed 5-<i>exo</i>-dig cyclization pathway. The products easily underwent photoinduced rearrangement to 3-amino-1-benzothiophene-1,1-diones (up to 35 % yi ...[more]

PMID: 30443160

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