Synthesis of methoxy-2-hydroxy1,4-naphthoquinones and reaction of one isomer with aldehydes under basic conditions

被引：17

作者：

Ameer, F

Giles, RGF

Green, IR

Pearce, R

机构：

[1] Univ Western Cape, Dept Chem, ZA-7530 Bellville, South Africa

[2] Murdoch Univ, Dept Chem, Murdoch, WA 6150, Australia

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

methoxy-2-hydroxy-1,4-naphthoquinones; methoxy-naphtho[2,3-b]pyran-5,10-diones; aldehydes; isomer;

D O I：

10.1081/SCC-120030312

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two protocols for the synthesis of methoxy-2-hydroxy-1,4-naphtho-quinones were investigated in order to evaluate their behavior towards aldehydes under amine-basic conditions. Both the nature of the quinone and aliphatic aldehyde contribute to the viability of this condensation as well as further transformations.

引用

收藏

页码：1247 / 1258

页数：12

相关论文

共 21 条

[1] The DDQ mediated cyclization products of some 2-hydroxy-3-(1′-alkenyl)-1,4-naphthoquinones [J].

Ameer, F ;

Giles, RGF ;

Green, IR ;

Nagabhushana, KS .

SYNTHETIC COMMUNICATIONS, 2002, 32 (03) :369-380

[2] NATURALLY OCCURRING QUINONES .6+ SPINOCHROME D [J].

ANDERSON, HA ;

SMITH, J ;

THOMSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :2141-&

[3] QUINONES .7. NEW ROUTES TO 2-HYDROXY-1,4-NAPHTHAQUINONES [J].

BAILLIE, AC ;

THOMSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (23) :2184-&

[4] A convenient synthesis of monpain trimethylether. [J].

Bekaert, A ;

Andrieux, J ;

Plat, M ;

Brion, JD .

TETRAHEDRON LETTERS, 1997, 38 (24) :4219-4220

[5] REACTION OF 2-HYDROXY-1,4-NAPHTHOQUINONE WITH ALDEHYDES - SYNTHESIS OF 2-HYDROXY-3-ALK-1-ENYLNAPHTHOQUINONES [J].

BOCK, K ;

JACOBSEN, N ;

TEREM, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (04) :659-664

[6] PIGMENTS OF GNOMONIA-ERYTHROSTOMA .1. STRUCTURES OF ERYTHROSTOMINONE, DEXOYERYTHROSTOMINONE, AND DEXOYERYTHROSTOMINOL [J].

CROSS, BE ;

TURNER, WB ;

EDINBERRY, MN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (03) :380-+

[7] Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts [J].

Cui, DM ;

Kawamura, M ;

Shimada, S ;

Hayashi, T ;

Tanaka, M .

TETRAHEDRON LETTERS, 2003, 44 (21) :4007-4010

[8] THE OXIDATION OF 1,5-DIHYDROXYNAPHTHALENE BY POTASSIUM SUPEROXIDE IN THE HETEROGENEOUS PHASE [J].

DEMIN, M ;

MAURETTE, MT ;

OLIVEROS, E ;

HOCQUAUX, M ;

JACQUET, B .

TETRAHEDRON, 1986, 42 (18) :4953-4962

[9] Synthesis of methoxy and hydroxy containing tetralones: versatile intermediates for the preparation of biologically relevant molecules [J].

Ghatak, A ;

Dorsey, JM ;

Garner, CM ;

Pinney, KG .

TETRAHEDRON LETTERS, 2003, 44 (21) :4145-4148

[10] SYNTHESES OF SUBSTITUTED 1,4-NAPHTHOQUINONES BY DIELS-ALDER ADDITION OF METHOXYCYCLOHEXADIENES TO SUBSTITUTED 1,4-BENZOQUINONES [J].

GILES, RGF ;

ROOS, GHP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (19) :2057-2060