Synthesis of 2-acetyl-5,8-dihydro-1,4-dihydroxy-3-methyl naphthalene: A product from the isomerisation of Diels-Alder adducts of both 5-methyl- and 6-methyl-2-acetyl-1,4-benzoquinone with 1,3-butadiene.

被引：6

作者：

Ahmad, FBH ^{[1
]}

Bruce, JM ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 07期

关键词：

D O I：

10.1080/00397919608003486

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Acetyl-5,8-dihydro-1,4-dihydroxy-3-methyl-naphthalene was synthesised via Diels-Alder addition of 2-acetyl-3-methyl-1,4-benzoquinone to buta-13-diene followed by enolisation. It was identical with material obtained by pyridine-induced acetyl migration from the 1,3-butadiene adducts of both 3- and 6-methyl-2-acetyl-1,4-benzoquinone.

引用

页码：1263 / 1271

页数：9

共 5 条

[1]

Ahmad F. B. H., 1989, PERTANIKA, V12, P219

[2] [1,5] AND [1,2] ACETYL SHIFTS IN DIELS-ALDER ADDUCTS OF 2-ACETYL-6-METHYL-1,4-BENZOQUINONE [J].

AHMAD, FBH ;

BRUCE, JM ;

KHALAFY, J ;

SABETIAN, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (04) :169-171

[3] ISOMERIZATION OF DIELS-ALDER ADDUCTS OF BENZOYL-1,4-BENZOQUINONES - A ROUTE TO THE ANTHRACYCLINONE RING-SYSTEM [J].

AHMAD, FBH ;

BRUCE, JM .

SYNTHETIC COMMUNICATIONS, 1994, 24 (12) :1639-1649

[4] A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].

ATTENBURROW, J ;

CAMERON, AFB ;

CHAPMAN, JH ;

EVANS, RM ;

HEMS, BA ;

JANSEN, ABA ;

WALKER, T .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111

[5]

HOWE CA, 1965, J CHEM SOC, P795

← 1 →