p-methoxybenzyl group as a protecting group of the nitrogen in indole derivatives: Deprotection by DDQ or trifluoroacetic acid

被引：24

作者：

Miki, Y ^{[1
]}

Hachiken, H ^{[1
]}

Kashima, Y ^{[1
]}

Sugimura, W ^{[1
]}

Yanase, N ^{[1
]}

机构：

[1] Kinki Univ, Fac Pharmaceut Sci, Higashiosaka, Osaka 577, Japan

来源：

HETEROCYCLES | 1998年 / 48卷 / 01期

关键词：

D O I：

10.3987/COM-97-7990

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotection of 9-p-methoxybenzylcarbazole with DDQ gave a carbazole. However, methyl 1-p-methoxybenzylindole-2-carboxylate and dimethyl 1-p-methoxybenzyl-2,3-indoledicarboxylate were treated with TFA to yield the corresponding methyl indole-2-carboxylate and dimethyl indole-2,3-dicarboxylate.

引用

页码：1 / 4

页数：4

共 14 条

[1] STUDIES ON V-TRIAZOLES .4. THE 4-METHOXYBENZYL GROUP, A VERSATILE N-PROTECTING GROUP FOR THE SYNTHESIS OF N-UNSUBSTITUTED V-TRIAZOLES [J].

BUCKLE, DR ;

ROCKELL, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :627-630

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3] SYNTHESIS OF A NOVEL PYRROLO[2,3-D]PYRIMIDINE ALKALOID, RIGIDIN [J].

EDSTROM, ED ;

WEI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :403-407

[4] PREPARATION OF 2-SUBSTITUTED PYRROLES AND INDOLES BY REGIOSELECTIVE ALKYLATION AND DEPROTECTION OF 1-(2-TRIMETHYLSILYLETHOXYMETHYL)PYRROLE AND 1-(2-TRIMETHYLSILYLETHOXYMETHYL) INDOLE [J].

EDWARDS, MP ;

DOHERTY, AM ;

LEY, SV ;

ORGAN, HM .

TETRAHEDRON, 1986, 42 (13) :3723-3729

[5]

GREEN TW, 1991, PROTECTIVE GROUPS OR

[6]

HIROTA K, 1986, TETRAHEDRON, V42, P3032

[7] SYNTHESIS OF PYRANO[4,3-B]INDOLES AS CONFORMATIONALLY RESTRICTED ANALOGS OF THE SEROTONIN ANTAGONIST ICS-205-930 AND AS PRECURSORS TO 2-VINYLINDOLES [J].

MACOR, JE ;

RYAN, K ;

NEWMAN, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4785-4795

[8] Synthesis and reactivity of pyrrolo[3,2-e]indole: Removal of a N-BOM group from an unactivated indole [J].

Macor, JE ;

Forman, JT ;

Post, RJ ;

Ryan, K .

TETRAHEDRON LETTERS, 1997, 38 (10) :1673-1676

[9] Reaction of indole-2,3-dicarboxylic anhydride with (3-bromo-4-pyridyl)triisopropoxytitanium: Synthesis of ellipticine [J].

Miki, Y ;

Tada, Y ;

Yanase, N ;

Hachiken, H ;

Matsushita, K .

TETRAHEDRON LETTERS, 1996, 37 (43) :7753-7754

[10]

MIKI Y, 1995, TETRAHEDRON LETT, V36, P1671

← 1 2 →