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1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

ABSTRACT: We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics.

SUBMITTER: Ikawa T

PROVIDER: S-EPMC6020534 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

Ikawa Takashi T Masuda Shigeaki S Takagi Akira A Akai Shuji S

Chemical science 20160418 8

We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds <i>via</i> reactions with arynophil ...[more]

PMID: 30155171

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