Synthesis of 3-substituted 4-hydroxyquinolin-2-ones via C-acylation reactions of active methylene compounds with functionalized 3,1-benzoxazin-4-ones

被引：0

作者：

Mitsos, C ^{[1
]}

Zografos, A ^{[1
]}

Igglessi-Markopoulou, O ^{[1
]}

机构：

[1] Natl Tech Univ Athens, Dept Chem Engn, Organ Chem Lab, GR-15773 Athens, Greece

来源：

HETEROCYCLES | 1999年 / 51卷 / 07期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for the construction of 4-hydroxyquinolin-2-ones is described. Benzoxazinones react with the anion of active methylene compounds to produce the functionalized C-acylation componnds in very good yields. These key intermediates are cyclized to the desired quinolinones (25-40) under basic conditions. Spectral data and physical characteristics for all compounds are reported.

引用

页码：1543 / +

页数：20

共 50 条

[1] REACTIONS WITH 3,1-BENZOXAZIN-4-ONES .3. REACTIONS OF 6,8-DIBROMO-2-METHYL-3,1-BENZOXAZIN-4-ONES WITH AMINES
ISMAIL, MF
SHAMS, NA
SALEM, MR
EMARA, SA
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23): : 4172 - 4174
[2] Reactions of 2-methyl-3,1-benzoxazin-4-one with active methylene compounds: A new route to 3-substituted 4-hydroxyquinolin-2(1H)-ones
Detsi, A
Bardakos, V
Markopoulos, J
IgglessiMarkopoulou, O
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24): : 2909 - 2913
[3] SYNTHESIS OF 2-SUBSTITUTED-4H-3,1-BENZOXAZIN-4-ONES
BAIN, DI
SMALLEY, RK
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (13): : 1593 - &
[4] STUDIES ON HYDROLYSIS OF 3,1-BENZOXAZIN-4-ONES
WILLIAMS, A
SALVADOR.G
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (06): : 1105 - &
[5] 3,1-BENZOXAZIN-4-ONES, 3,1-BENZOTHIAZIN-4-ONES AND N-ARYLCYANOTHIOFORMAMIDES
BESSON, T
EMAYAN, K
REES, CW
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (14) : 1419 - 1420
[6] Synthesis and reactions of 2-hetero-4H-3,1-benzoxazin-4-ones
Coppola, GM
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1369 - 1388
[7] 4H-3,1-BENZOXAZIN-4-ONES METHOXY-SUBSTITUTED 2-(2-ARENSULPHONYLAMINOPNENYL( -4H-3,1-BENZOXAZIN-4-ONES
LOSEVA, MV
BOLOTIN, BM
KRASOVIT.BM
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (08): : 1028 - &
[8] STRUCTURE AND SOLID HYDROLYSIS OF 3,1-BENZOXAZIN-4-ONES
VICENS, J
DECORET, C
GAGET, C
ETTER, MC
ERREDE, LA
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1983, 96 (1-4): : 39 - 43
[9] 3,1-BENZOTHIAZIN-4-ONES AND 3,1-BENZOXAZIN-4-ONES - HIGHLY DIFFERENT ACTIVITIES IN CHYMOTRYPSIN INACTIVATION
NEUMANN, U
GUTSCHOW, M
BIOORGANIC CHEMISTRY, 1995, 23 (01) : 72 - 88
[10] THE SYNTHESIS OF A NOVEL SERIES OF SUBSTITUTED 2-PHENYL-4H-3,1-BENZOXAZIN-4-ONES
PAVLIDIS, VH
PERRY, PJ
SYNTHETIC COMMUNICATIONS, 1994, 24 (04) : 533 - 548

← 1 2 3 4 5 →