Radical mediated synthesis of 6-arylphenanthridines via benzotriazole ring-opening

被引：22

作者：

Katritzky, AR

Yang, BZ

机构：

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 03期

关键词：

D O I：

10.1002/jhet.5570330313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation of diarylbenzotriazol-1-ylmethanes followed by addition of copper(I) iodide gave 6-arylphenanthridine derivatives in moderate yields. When the two aryl groups were the same or contained very different electron densities, only one product was obtained. However, when the two aryl groups exhibited electron densities of similar magnitude, two isomers were afforded. According to the substituent effect, we believe that the reactions proceed via radical intermediates formed by copper(I) iodide.

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页码：607 / 610

页数：4

相关论文

共 15 条

[1] REACTIONS OF ORGANIC AZIDES .3. THE SYNTHESIS OF PHENANTHRIDINES BY THE INTERACTION OF FLUOREN-9-OLS WITH HYDRAZOIC AND SULPHURIC ACIDS, AND THE MECHANISM OF THE REARRANGEMENT OF THE INTERMEDIATE AZIDES [J].

ARCUS, CL ;

COOMBS, MM .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (DEC) :4319-4329

[2] COMPARISON OF PHENANTHRIDINE WITH OTHER AZA-AROMATIC HETEROCYCLES [J].

EISCH, J ;

GILMAN, H .

CHEMICAL REVIEWS, 1957, 57 (03) :525-581

[3] APPLICATION OF THE BRUCKNER METHOD TO THE SYNTHESIS OF PHENANTHRIDINE DERIVATIVES [J].

GOVINDACHARI, TR ;

NAGARAJAN, K ;

PAI, BR ;

ARUMUGAM, N .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4280-4283

[4] SOME DERIVATIVES OF BIPHENYL AND OF PHENANTHRIDINE [J].

HOLLINGSWORTH, B ;

PETROW, V .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (SEP) :3771-+

[5] STUDIES ON THE THERMAL-ISOMERIZATION OF N-ARYLMETHYLBENZOTRIAZOLES [J].

KATRITZKY, AR ;

PERUMAL, S ;

FAN, WQ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (12) :2059-2062

[6] On the synthesises of some isomeric ethyl-phenanthridines. [J].

Kondo, H ;

Uyeo, S .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1937, 70 :1094-1097

[7]

LEARDINI R, 1985, SYNTHESIS-STUTTGART, P107

[8]

MAYO PD, 1950, NATURE, V166, P1075

[9] Researches in the phenanthridine series Part V The colour and antiseptic properties of quaternary salts [J].

Morgan, G ;

Walls, LP ;

Browning, CH ;

Gulbransen, R ;

Robb, JVM .

JOURNAL OF THE CHEMICAL SOCIETY, 1938, :389-397

[10] SYNTHETIC APPLICATION OF LITHIATION REACTIONS .14. NOVEL SYNTHESIS OF 7,8-DIMETHOXY PHENANTHRIDINE [J].

NARASIMHAN, NS ;

CHANDRACHOOD, PS ;

SHETE, NR .

TETRAHEDRON, 1981, 37 (04) :825-827