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Synthesis of Benzofuran Derivatives via a DMAP-Mediated Tandem Cyclization Reaction Involving ortho-Hydroxy α-Aminosulfones.

ABSTRACT: An efficient cascade cyclization strategy was developed to synthesize aminobenzofuran spiroindanone and spirobarbituric acid derivatives utilizing 2-bromo-1,3-indandione, 5-bromo-1,3-dimethylbarbituric acid, and ortho-hydroxy α-aminosulfones as substrates. Under the optimized reaction conditions, the corresponding products were obtained with high efficiency, exceeding 95% and 85% yields for the respective derivatives. This protocol demonstrates exceptional substrate versatility and robust scalability up to the Gram scale, establishing a stable platform for the synthesis of 3-aminobenzofuran derivative. The successful synthesis paves the way for further biological evaluations with potential implications in scientific research.

SUBMITTER: Zhu RR

PROVIDER: S-EPMC11357171 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Benzofuran Derivatives via a DMAP-Mediated Tandem Cyclization Reaction Involving <i>ortho</i>-Hydroxy α-Aminosulfones.

Zhu Rong-Rong RR Hou Xi-Qiang XQ Du Da-Ming DM

Molecules (Basel, Switzerland) 20240806 16

An efficient cascade cyclization strategy was developed to synthesize aminobenzofuran spiroindanone and spirobarbituric acid derivatives utilizing 2-bromo-1,3-indandione, 5-bromo-1,3-dimethylbarbituric acid, and <i>ortho</i>-hydroxy α-aminosulfones as substrates. Under the optimized reaction conditions, the corresponding products were obtained with high efficiency, exceeding 95% and 85% yields for the respective derivatives. This protocol demonstrates exceptional substrate versatility and robust ...[more]

PMID: 39202804

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