REGIOSELECTIVE OXIDATIVE AMINATION OF 3-CARBOMETHOXYINDOLE-4,7-QUINONES

被引：6

作者：

EDSTROM, ED

JONES, Z

机构：

[1] Department of Chemistry and Biochemistry, Utah State University Logan

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期

关键词：

D O I：

10.1016/0040-4039(95)01458-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative addition of benzhydryl amine and azide ion to N-methyl-3-carbomethoxyindole-4,7-quinones has been determined. For the C-5, C-6 unsubstituted system 5, an 8:1 preference for the C-5 isomer was achieved. The regiochemically defined 6-amino isomer was made by reacting 5-bromoindolequinone 10 with benzhydrylamine followed by removal. of the diphenylmethyl and bromo groups. A new equivalent for introducing ammonia into indolequinones has been developed.

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页码：7039 / 7042

页数：4

相关论文

共 24 条

[1] THE ADDITION OF DIMETHYLAMINE TO BENZOQUINONE [J].

BALTZLY, R ;

LORZ, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (02) :861-862

[2] INTRAMOLECULAR CYCLOADDITION REACTIONS OF DIENYL NITROSO-COMPOUNDS - APPLICATION TO THE SYNTHESIS OF MITOMYCIN-K [J].

BENBOW, JW ;

MCCLURE, KF ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12305-12314

[3]

COOP BR, 1991, J ORG CHEM, V56, P4596

[4]

EDSTROM ED, 1995, SYNLETT, P49

[5] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1993, 10 (05) :497-539

[6]

FINLEY KT, 1974, CHEM QUINONOID COMPO, pCH17

[7] PRACTICAL TOTAL SYNTHESIS OF (+/-)-MITOMYCIN-C [J].

FUKUYAMA, T ;

YANG, LH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8303-8304

[8] AMINE ADDITION TO UNSYMMETRICAL BENZOQUINONES [J].

LULY, JR ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2745-2752

[9] SYNTHESIS OF PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR HECK REACTION OF N-(2-BROMOARYL) ENAMINONES [J].

MICHAEL, JP ;

CHANG, SF ;

WILSON, C .

TETRAHEDRON LETTERS, 1993, 34 (51) :8365-8368

[10] SYNTHESIS OF THE NATURALLY-OCCURRING INDOLEQUINONE BE-10988, AN INHIBITOR OF TOPOISOMERASE-2 [J].

MOODY, CJ ;

SWANN, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2561-2565