A Sequential Cycloisomerization/Oxidative Aromatization of 2-Propargyl-cyclohexenones for Direct Access to Substituted Benzofurans

Chada Raji Reddy; Ketan Wadekar; Karna Nair; Y. Lakshmi Prapurna

doi:10.1055/a-1863-4082

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(20): 4503-4508
DOI: 10.1055/a-1863-4082

paper

A Sequential Cycloisomerization/Oxidative Aromatization of 2-Propargyl-cyclohexenones for Direct Access to Substituted Benzofurans

Chada Raji Reddy ∗

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

,

Ketan Wadekar

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

,

Karna Nair

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

,

Y. Lakshmi Prapurna

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India

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Abstract

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CSIR-IICT Communication No. IICT/Pubs./2022/084

Abstract

A new approach for the synthesis of benzofurans starting from non-aromatic precursors is reported. The reaction involves sequential DBU-mediated cycloisomerization for furanylation followed by benzene ring construction via oxidative aromatization in the presence of Oxone®. Atom- and pot-economy, simple reaction conditions, the straightforward preparation of starting materials and access to diverse substituted benzofurans are the major advantages of this reaction.

Key words

cyclohexenones - cycloisomerization - Oxone® - oxidative aromatization - benzofurans

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Referenzen

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