Highly efficient photochemical generation of o-quinone methide from Mannich bases of phenol derivatives

被引：71

作者：

Nakatani, K ^{[1
]}

Higashida, N ^{[1
]}

Saito, I ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM & BIOL CHEM,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(97)01071-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

o-Quinone methide was efficiently produced by photoirradiation of phenolic Mannich bases in aqueous acetonitrile with low energy UV light. The photoreaction proceeds most effectively at neutral pH in aqueous solvents. (C) 1997 Elsevier Science Ltd.

引用

页码：5005 / 5008

页数：4

共 9 条

[1] BOGER DL, 1987, HETERO DIELSALDER ME, P167
[2] INDUCIBLE ALKYLATION OF DNA USING AN OLIGONUCLEOTIDE QUINONE CONJUGATE
CHATTERJEE, M
ROKITA, SE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6397 - 6399
[3] THE ROLE OF A QUINONE METHIDE IN THE SEQUENCE-SPECIFIC ALKYLATION OF DNA
CHATTERJEE, M
ROKITA, SE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 1690 - 1697
[4] QUINONE METHIDE INTERMEDIATES FROM THE PHOTOLYSIS OF HYDROXYBENZYL ALCOHOLS IN AQUEOUS-SOLUTION
DIAO, L
YANG, C
WAN, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) : 5369 - 5370
[5] PHOTOGENERATION OF HIGHLY ELECTROPHILIC BENZOYLKETENE FROM DIBENZOYLDIAZOMETHANE IN AQUEOUS SOLVENTS - REACTION WITH AMINO-ACIDS AND DNA CLEAVAGE
NAKATANI, K
SHIRAI, J
TAMAKI, R
SAITO, I
[J]. TETRAHEDRON LETTERS, 1995, 36 (30) : 5363 - 5366
[6] PHOTOGENERATION OF CARBOCATION VIA INTRAMOLECULAR ELECTRON-TRANSFER - PHOTOINDUCED DNA ALKYLATION
SAITO, I
TAKAYAMA, M
SAKURAI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2653 - 2654
[7] TOMASZ M, 1992, ADV DNA SEQUENCE SPE, V1, P247
[8] 1995 Merck Frosst Award Lecture - Quinone methides: Relevant intermediates in organic chemistry
Wan, P
Barker, B
Diao, L
Fischer, M
Shi, YJ
Yang, C
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (04): : 465 - 475
[9] Tandem quinone methide generation for cross-linking DNA
Zeng, QP
Rokita, SE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9080 - 9081

← 1 →