TY - JOUR
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 - http://www.scopus.com/inward/record.url?scp=33749515228&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2006.08.090
DO - 10.1016/j.tet.2006.08.090
M3 - Article
AN - SCOPUS:33749515228
VL - 62
SP - 10945
EP - 10953
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 47
ER -