New synthetic approaches to fused polyheterocyclic compounds by using domino cyclization reactions of aromatic diyne and enyne systems

Ryo Irie, Masaki Furusawa, Kosuke Arita, Kazunobu Igawa, Katsuhiko Tomooka

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2 Citations (Scopus)

Abstract

Oxa-heterocyclic compounds such as benzofurans, chromenes, and chromanes constitute a diverse array of biologically active materials. Furthermore, extended π-conjugated systems, in which oxa-heteroaromalic and benzene rings are condensed alternately, have been exploited as components of photoelectronic devices. Thus, the development of efficient synthetic approaches toward these valuable classes of heterocycles has been pursued. Among those precedented hetero-cyclization methods, domino cyclodehydrogenation and cycloisomerization reactions are highly attractive as they could produce elaborate heterocyclic frameworks from readily available starting materials in an atom-efficient manner. Herein, we wish to report the novel multimode domino ring-forming reactions of o-phenylenediyne-linked bis(arenol)s (aromatic diyne systems) and its analogous aromatic enyne systems to provide unique fused oxa-heterocycles, which are otherwise difficult to synthesize.

Original languageEnglish
Pages (from-to)1131-1142
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume72
Issue number10
DOIs
Publication statusPublished - Oct 1 2014

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Cyclization
Benzofurans
Benzopyrans
Heterocyclic Compounds
Benzene
Atoms

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "New synthetic approaches to fused polyheterocyclic compounds by using domino cyclization reactions of aromatic diyne and enyne systems",
abstract = "Oxa-heterocyclic compounds such as benzofurans, chromenes, and chromanes constitute a diverse array of biologically active materials. Furthermore, extended π-conjugated systems, in which oxa-heteroaromalic and benzene rings are condensed alternately, have been exploited as components of photoelectronic devices. Thus, the development of efficient synthetic approaches toward these valuable classes of heterocycles has been pursued. Among those precedented hetero-cyclization methods, domino cyclodehydrogenation and cycloisomerization reactions are highly attractive as they could produce elaborate heterocyclic frameworks from readily available starting materials in an atom-efficient manner. Herein, we wish to report the novel multimode domino ring-forming reactions of o-phenylenediyne-linked bis(arenol)s (aromatic diyne systems) and its analogous aromatic enyne systems to provide unique fused oxa-heterocycles, which are otherwise difficult to synthesize.",
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T1 - New synthetic approaches to fused polyheterocyclic compounds by using domino cyclization reactions of aromatic diyne and enyne systems

AU - Irie, Ryo

AU - Furusawa, Masaki

AU - Arita, Kosuke

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

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N2 - Oxa-heterocyclic compounds such as benzofurans, chromenes, and chromanes constitute a diverse array of biologically active materials. Furthermore, extended π-conjugated systems, in which oxa-heteroaromalic and benzene rings are condensed alternately, have been exploited as components of photoelectronic devices. Thus, the development of efficient synthetic approaches toward these valuable classes of heterocycles has been pursued. Among those precedented hetero-cyclization methods, domino cyclodehydrogenation and cycloisomerization reactions are highly attractive as they could produce elaborate heterocyclic frameworks from readily available starting materials in an atom-efficient manner. Herein, we wish to report the novel multimode domino ring-forming reactions of o-phenylenediyne-linked bis(arenol)s (aromatic diyne systems) and its analogous aromatic enyne systems to provide unique fused oxa-heterocycles, which are otherwise difficult to synthesize.

AB - Oxa-heterocyclic compounds such as benzofurans, chromenes, and chromanes constitute a diverse array of biologically active materials. Furthermore, extended π-conjugated systems, in which oxa-heteroaromalic and benzene rings are condensed alternately, have been exploited as components of photoelectronic devices. Thus, the development of efficient synthetic approaches toward these valuable classes of heterocycles has been pursued. Among those precedented hetero-cyclization methods, domino cyclodehydrogenation and cycloisomerization reactions are highly attractive as they could produce elaborate heterocyclic frameworks from readily available starting materials in an atom-efficient manner. Herein, we wish to report the novel multimode domino ring-forming reactions of o-phenylenediyne-linked bis(arenol)s (aromatic diyne systems) and its analogous aromatic enyne systems to provide unique fused oxa-heterocycles, which are otherwise difficult to synthesize.

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