Reaction of 4‑(Alkynyloxy)cyclohexa-2,5-dienones\nwith Dimethyl Sulfoxide: A Catalyst-Free Formation of 6/5/3-Fused\nTricyclic Enones

6/5/3-Fused\ntricyclic enones were obtained when 4-(alkynyloxy)cyclohexa-2,5-dienones\nwere treated with DMSO at 150 °C. The reaction proceeded via\na four-membered oxathietene intermediate. The protocol developed is\natom economical, has a broad substrate scope, and is amenable to gram-scale\nsynthesis. The products obtained are susceptible to further synthetic\ntransformations.

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.joc.4c02553.s001
Primary Topic
Synthesis of heterocyclic compounds
Type
article
Field-Weighted Citation Impact
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article

Reaction of 4‑(Alkynyloxy)cyclohexa-2,5-dienones\nwith Dimethyl Sulfoxide: A Catalyst-Free Formation of 6/5/3-Fused\nTricyclic Enones

Figshare
Synthesis of heterocyclic compounds
article

Reaction of 4‑(Alkynyloxy)cyclohexa-2,5-dienones\nwith Dimethyl Sulfoxide: A Catalyst-Free Formation of 6/5/3-Fused\nTricyclic Enones

article en

Abstract

6/5/3-Fused\ntricyclic enones were obtained when 4-(alkynyloxy)cyclohexa-2,5-dienones\nwere treated with DMSO at 150 °C. The reaction proceeded via\na four-membered oxathietene intermediate. The protocol developed is\natom economical, has a broad substrate scope, and is amenable to gram-scale\nsynthesis. The products obtained are susceptible to further synthetic\ntransformations.

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Openalex Percentile: Top 75%
Synthesis of heterocyclic compounds
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