Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles

Christopher D. Gabbutt, Tessa F.L. Hargrove, B. Mark Heron, David Jones, Carley Poyner, Emel Yildiz, Peter N. Horton, Michael B. Hursthouse

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The oxidation of 3-[bis-(diaryl)methyl]chromones 2 with p-chloranil affords novel acetals, 3-[bis-(diaryl)methylene]-2-methoxychroman-4-ones, 4 through interception of a pyrylium type intermediate. Oxidation of 3-(2-hydroxyphenyl)-4-[bis-(diaryl)methyl]pyrazoles 8, derived from 2 and hydrazines, gave 4,4-diarylbenzopyrano[4,3-c]pyrazoles 15. The electronic absorption spectra of 4 and 15 upon protonation are comparable with those of triarylmethine cationic dyes.

Original languageEnglish
Pages (from-to)10945-10953
Number of pages9
JournalTetrahedron
Volume62
Issue number47
Early online date25 Sep 2006
DOIs
Publication statusPublished - 20 Nov 2006
Externally publishedYes

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Pyrazoles
Cations
Chloranil
Hydrazines
Chromones
Acetals
Oxidation
Protonation
Absorption spectra
Coloring Agents

Cite this

Gabbutt, Christopher D. ; Hargrove, Tessa F.L. ; Mark Heron, B. ; Jones, David ; Poyner, Carley ; Yildiz, Emel ; Horton, Peter N. ; Hursthouse, Michael B. / Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles. In: Tetrahedron. 2006 ; Vol. 62, No. 47. pp. 10945-10953.
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abstract = "The oxidation of 3-[bis-(diaryl)methyl]chromones 2 with p-chloranil affords novel acetals, 3-[bis-(diaryl)methylene]-2-methoxychroman-4-ones, 4 through interception of a pyrylium type intermediate. Oxidation of 3-(2-hydroxyphenyl)-4-[bis-(diaryl)methyl]pyrazoles 8, derived from 2 and hydrazines, gave 4,4-diarylbenzopyrano[4,3-c]pyrazoles 15. The electronic absorption spectra of 4 and 15 upon protonation are comparable with those of triarylmethine cationic dyes.",
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Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles. / Gabbutt, Christopher D.; Hargrove, Tessa F.L.; Mark Heron, B.; Jones, David; Poyner, Carley; Yildiz, Emel; Horton, Peter N.; Hursthouse, Michael B.

In: Tetrahedron, Vol. 62, No. 47, 20.11.2006, p. 10945-10953.

Research output: Contribution to journalArticle

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AU - Jones, David

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AU - Hursthouse, Michael B.

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