BENZYL GROUP MIGRATION IN 9-METHYL-10-BENZYL-9,10-DIHYDROACRIDINE

被引：4

作者：

DIGENIS, GA

机构：

[1] Department of Pharmaceutical Chemistry and Materia Medica, College of Pharmacy, University of Kentucky, Lexington, Kentucky

来源：

JOURNAL OF PHARMACEUTICAL SCIENCES | 1969年 / 58卷 / 03期

关键词：

9‐Methyl‐10‐benzyl‐9,10‐dihydroacridine—benzyl group migration; IR spectrophotometry—structure; identity; NMR spectroscopy—structure; N‐Butyl lithium effect—9‐methyl‐10‐benzylacridine; UV spectrophotometry—structure;

D O I：

10.1002/jps.2600580310

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

When 9‐methyl‐10‐benzylacridane was treated with n‐butyl lithium, its benzyl group was found to migrate to the 9‐position. NMR and deuterium oxide‐exchange studies suggested that the rearrangement occurred intramolecularly. No rearrangement was noticed when 9‐methyl‐10‐methylacridane was treated similarly. When N,N‐dimethyl‐9‐carboxamido‐9,10‐dimethylacridane was treated with LiAlH4 its carboxamido function was displaced and 9,10‐dimethylacridane was produced. Copyright © 1969 Wiley‐Liss, Inc., A Wiley Company

引用

页码：335 / &

共 4 条

[1] Antispasmodics. II. Basic esters of some polynuclear carboxylic acids [J].

Burtner, RR ;

Cusic, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1582-1585

[2] The quantitative analysis of alkyllithium compounds [J].

Gilman, H ;

Haubein, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1515-1516

[3] NOTIZ ZUR KENNTNIS DER ACRIDINIUMSALZE [J].

KROHNKE, F ;

HONIG, HL .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10) :2226-2227

[4] The preparation of acridanes by the Grignard reaction [J].

Semon, WL ;

Craig, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :1278-1282

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