STUDIES DIRECTED TOWARDS TOTAL SYNTHESES OF THE TROPOLOISOQUINOLINE ALKALOIDS GRANDIRUBRINE AND IMERUBRINE .2. THERMOLYSIS OF 8,9-DIHYDRO-2-HYDROXY-3,10,11,12-TETRAMETHOXYISOQUINO[2,1-C][1,2,3]BENZOTRIAZIN-7-IUM CHLORIDE - COMPETITIVE MODES OF CYCLIZATION LEADING TO THE INDENO[1,2,3-IJ]ISOQUINOLINE (AZAFLUORANTHENE) SKELETON

被引：10

作者：

BANWELL, MG

HAMEL, E

IRELAND, NK

MACKAY, MF

SERELIS, AK

机构：

[1] NCI,DCT,DTP,MOLEC PHARMACOL LAB,BETHESDA,MD 20892

[2] ICI DULUX,EXPLORATORY CHEM LABS,CLAYTON,VIC 3168,AUSTRALIA

[3] LA TROBE UNIV,DEPT CHEM,BUNDOORA,VIC 3083,AUSTRALIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 16期

关键词：

D O I：

10.1039/p19930001905

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis of the title compound 8 produced not only the expected azafluoranthene 7 but also the regioisomeric compound 23 and its dihydro counterpart 22. A mechanism for the formation of compounds 7, 22 and 23 from precursor 8 has been advanced. Reaction of salt 8 with copper bronze in aqueous sulfuric acid produced good yields of dihydroazafluoranthene 29 together with small amounts of the reduction product 30. The tubulin binding properties of the azafluoranthenes 7, 22, 23, 24 and 29 have been determined.

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页码：1905 / 1911

页数：7

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