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

doi:10.1016/j.tet.2006.08.090

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 journal › Article › peer-review

10 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 language	English
Pages (from-to)	10945-10953
Number of pages	9
Journal	Tetrahedron
Volume	62
Issue number	47
Early online date	25 Sept 2006
DOIs	https://doi.org/10.1016/j.tet.2006.08.090
Publication status	Published - 20 Nov 2006
Externally published	Yes

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Gabbutt, C. D., Hargrove, T. F. L., Mark Heron, B., Jones, D., Poyner, C., Yildiz, E., Horton, P. N., & Hursthouse, M. B. (2006). Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles. Tetrahedron, 62(47), 10945-10953. https://doi.org/10.1016/j.tet.2006.08.090

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

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.",

author = "Gabbutt, \{Christopher D.\} and Hargrove, \{Tessa F.L.\} and \{Mark Heron\}, B. and David Jones and Carley Poyner and Emel Yildiz and Horton, \{Peter N.\} and Hursthouse, \{Michael B.\}",

year = "2006",

month = nov,

day = "20",

doi = "10.1016/j.tet.2006.08.090",

language = "English",

volume = "62",

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journal = "Tetrahedron",

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T1 - Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles

AU - Gabbutt, Christopher D.

AU - Hargrove, Tessa F.L.

AU - Mark Heron, B.

AU - Jones, David

AU - Poyner, Carley

AU - Yildiz, Emel

AU - Horton, Peter N.

AU - Hursthouse, Michael B.

PY - 2006/11/20

Y1 - 2006/11/20

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/33749515228

U2 - 10.1016/j.tet.2006.08.090

DO - 10.1016/j.tet.2006.08.090

M3 - Article

AN - SCOPUS:33749515228

SN - 0040-4020

VL - 62

SP - 10945

EP - 10953

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

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

Abstract

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