TUNGSTATE-CATALYZED OXIDATION OF TETRAHYDROQUINOLINES WITH HYDROGEN-PEROXIDE - A NOVEL METHOD FOR THE SYNTHESIS OF CYCLIC HYDROXAMIC ACIDS

被引：50

作者：

MURAHASHI, SI

ODA, T

SUGAHARA, T

MASUI, Y

机构：

[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 06期

关键词：

D O I：

10.1021/jo00293a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sodium tungstate catalyzed oxidation of 1,2,3,4-tetrahydroquinolines (1) with 30& aqueous hydrogen peroxide solution in methanol gives l-hydroxy-3,4-dihydroquinolin-2(lH)-ones (2), which are important biologically active compounds, in good to excellent yields. The cyclic hydroxamic acid 7 is also obtained in good yield. Since reduction of 2 thus obtained gives 3,4-dihydroquinolin-2(lH)-ones (4), the present reaction provides a convenient method for synthesis of 4 from 1. © 1990, American Chemical Society. All rights reserved.

引用

页码：1744 / 1749

页数：6

共 50 条

[1] THE SYNTHESIS OF 1-BENZAZEPINE DERIVATIVES AS MODEL COMPOUNDS RELATED TO APO-BETA-ERYTHROIDINE .12.
ASTILL, BD
BOEKELHEIDE, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (15) : 4079 - 4084
[2] OXIDATION OF AMINES BY A 4A-HYDROPEROXYFLAVIN
BALL, S
BRUICE, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) : 6498 - 6503
[3] 4A-HYDROPEROXYFLAVIN N-OXIDATION OF TERTIARY-AMINES
BALL, S
BRUICE, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) : 4017 - 4019
[4] BAPAT JB, 1969, ADV HETEROCYCLIC CHE, V10, P199
[5] CHEMISTRY OF HYDROXAMIC ACIDS AND N-HYDROXYIMIDES
BAUER, L
EXNER, O
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) : 376 - 384
[6] SELECTIVE REDUCTION OF ALPHA-BETA-OLEFINIC AMIDES AND LACTAMS BY MAGNESIUM AND METHANOL
BRETTLE, R
SHIBIB, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (11): : 2912 - 2919
[7] A synthesis of dihydrocarbostyril and homodihydroearbstyril by ring enlargentent and a synthesis of tetrahydroquinoline.
Briggs, LH
De Ath, GC
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1937, : 456 - 457
[8] 1-ALKYL-1,2,3,4-TETRAHYDROQUINOXALINES
CAVAGNOL, JC
WISELOGLE, FY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (04) : 795 - 799
[9] SOME CYCLIC HYDROXAMIC ACIDS
COUTTS, RT
NOBLE, D
WIBBERLEY, DG
[J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1964, 16 (12) : 773 - &
[10] SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF SOME CHLORO ANALOGS OF 3-AMINO-3,4-DIHYDRO-1-HYDROXYCARBOSTYRIL
DAVIS, AL
CHAMBERS, WH
KELLEY, DH
FELL, DA
HAYNES, JR
HULME, KL
GAGE, LD
MCCORD, TJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (07) : 752 - 755

← 1 2 3 4 5 →