Efficient synthesis of aminonaphthoquinones and azidobenzohydroquinones: Mechanistic considerations of the reaction of hydrazoic acid with quinones, an overview

被引：61

作者：

Couladouros, EA ^{[1
]}

Plyta, ZF ^{[1
]}

Haroutounian, SA ^{[1
]}

Papageorgiou, VP ^{[1
]}

机构：

[1] ARISTOTELIAN UNIV THESSALONIKI,DEPT CHEM ENGN,ORGAN CHEM LAB,GR-54006 THESSALONIKI,GREECE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 01期

关键词：

D O I：

10.1021/jo9614708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Parameters useful to predict and control the reaction outcome of conjugate addition of hydrazoic acid to quinones have been studied, and the optimum conditions for the efficient synthesis of aminonaphthoquinones and azidobenzohydroquinones are reported. The application of this reaction for the efficient formal synthesis of dephostatin is also presented.

引用

页码：6 / 10

页数：5

共 56 条

[1] DIRECT OBSERVATION OF THE REACTION OF THE QUINONE-METHIDE FROM 5,6-DIHYDROXYINDOLE WITH THE NUCLEOPHILIC AZIDE ION [J].

ALKAZWINI, AT ;

ONEILL, P ;

CUNDALL, RB ;

ADAMS, GE ;

JUNINO, A ;

MAIGNAN, J .

TETRAHEDRON LETTERS, 1992, 33 (21) :3045-3048

[2]

APOSTOLOPOULOS CD, 1994, LIEBIGS ANN CHEM, V8, P781

[3]

AWAD WJ, 1963, TETRAHEDRON, V19, P159

[4]

BARNISH IT, 1992, J CHEM RES-S, P208

[5]

BASHYAL BP, 1986, TETRAHEDRON LETT, V27, P3203

[6] THERMAL REACTIVITY OF TRICYCLIC 4,5-DIACYLTRIAZOLINES RESULTING FROM ADDITION OF ARYL AZIDES TO 1,4-NAPHTHOQUINONE AND 2-METHYL-1,4-NAPHTHOQUINONE [J].

BENATI, L ;

MONTEVECCHI, PC ;

SPAGNOLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :71-77

[7]

BITTNER S, 1994, SYNTHESIS-STUTTGART, P917

[8] TOTAL SYNTHESIS OF LAVENDAMYCIN METHYL-ESTER [J].

BOGER, DL ;

DUFF, SR ;

PANEK, JS ;

YASUDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5790-5795

[9] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF HETEROCYCLIC AZA DIENES - STUDIES ON THE TOTAL SYNTHESIS OF LAVENDAMYCIN - INVESTIGATIVE STUDIES ON THE PREPARATION OF THE CDE BETA-CARBOLINE RING-SYSTEM AND AB QUINOLINE-5,8-QUINONE RING-SYSTEM [J].

BOGER, DL ;

DUFF, SR ;

PANEK, JS ;

YASUDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5782-5789

[10] ADDITION OF HYDRAZOIC ACID TO CONJUGATED SYSTEMS [J].

BOYER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (11) :5248-5252

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