BEHAVIOR OF 2-CARBOMETHOXY- AND 2-ACETYL-1,4-BENZOQUINONE IN NENITZESCU INDOLE SYNTHESIS

被引：30

作者：

ALLEN, GR

WEISS, MJ

机构：

[1] Process and Preparations Research Section, Lederle Laboratories Division, American Cyanamid Company, Pearl River

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 01期

关键词：

D O I：

10.1021/jo01265a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2-carbomethoxy-1,4-benzoquinone (1) with ethyl 3-aminocrotonate (2a) gave ethyl trans-3-amino- 2-(2-carbomethoxy-3,6-dihydroxyphenyl)crotonate (3). This Michael-type adduct was transformed into ethyl 4-carbomethoxy-5-hydroxy-2-methylindole-3-carboxylate (4) and ethyl 5,8-dihydroxy-3-methylisocarbostyril- 4-carboxylate (5) when treated with 1 under equilibrating conditions. 2-Acetyl-1,4-benzoquinone (8) reacted with 2a and t-butyl 3-aminocrotonate (2b) to give the ethyl (9a) and t-butyl (9b) esters, respectively, of 5,8-dihydroxy-1,3-dimethylisoquinoline-4-carboxylic acid. © 1968, American Chemical Society. All rights reserved.

引用

页码：198 / &

共 12 条

[1] MITOMYCIN ANTIBIOTICS . SYNTHETIC STUDIES .14. NENITZESCU INDOLE SYNTHESIS . FORMATION OF ISOMERIC INDOLES AND REACTION MECHANISM [J].

ALLEN, GR ;

PIDACKS, C ;

WEISS, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (11) :2536-&

[2] THE CHEMISTRY OF THE MELANINS .3. THE SYNTHESIS OF HYDROXYINDOLES FROM PARA-BENZOQUINONES [J].

BEER, RJS ;

CLARKE, K ;

DAVENPORT, HF ;

ROBERTSON, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (AUG) :2029-2032

[3]

CASON J, 1948, ORG REACTIONS, V4, P354

[4]

Chatterjea J. N., 1966, J INDIAN CHEM SOC, V43, P633

[5] NUCLEAR MAGNETIC RESONANCE STUDIES OF KETO-ENOL EQUILIBRIA .5. ISOMERIZATION IN ALIPHATIC SCHIFF BASES [J].

DUDEK, GO ;

VOLPP, GP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (18) :2697-&

[6] SYNTHESIS OF 3-METHYL ISOQUINOLINES [J].

GOVINDACHARI, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (10) :1253-1262

[7] SYNTHETIC ANALOGS OF CORTICAL HORMONES .1. HOMOGENTISIC ACID AND ALPHA,2,5-TRIHYDROXYACETOPHENONE DERIVATIVES FROM 2,5-DIACETOXY-ALPHA-DIAZOACETOPHENONE [J].

KLOETZEL, MC ;

DAYTON, RP ;

ABADIR, BY .

JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (01) :38-49

[8]

Nenitzescu C. D., 1929, B SOC CHIM ROMANIA, V11, P37

[9]

NENITZESCU CD, 1930, CA 110, V24

[10]

RAILEANU D, 1965, REV ROUM CHIM, V10, P339

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