Regioselective nitration of 3-acetylindole and its N-acyl and N-sulfonyl derivatives.

被引：14

作者：

Ottoni, O ^{[1
]}

Cruz, R ^{[1
]}

Krammer, NH ^{[1
]}

机构：

[1] Univ Brasilia, Dept Quim, BR-70919970 Brasilia, DF, Brazil

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(98)02636-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Acetylindole reacts regioselectively with NO2BF4 in the presence of SnCl4 to produce 3-acetyl-5-nitroindole or 3-acetyl-6-nitroindole, depending an the temperature, both in excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1117 / 1120

页数：4

共 5 条

[1]

BERTI H, 1964, TETRAHEDRON, V20, P1397

[2] SYNTHETIC STUDIES ON TELEOCIDIN .1. REGIOSELECTIVE INTRODUCTION OF 4-AMINO AND 7-ACYL GROUPS ON INDOLE DERIVATIVE [J].

NAKATSUKA, S ;

MASUDA, T ;

ASANO, O ;

TERAMAE, T ;

GOTO, T .

TETRAHEDRON LETTERS, 1986, 27 (36) :4327-4330

[3] NITRATION OF INDOLES .V. NITRATION OF ELECTRONEGATIVELY SUBSTITUTED INDOLES . SYNTHESIS OF 4 BZ,3-DINITROINDOLES [J].

NOLAND, WE ;

RUSH, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :70-&

[4] Efficient and simple methods for the introduction of the sulfonyl, acyl and alkyl protecting groups on the nitrogen of indole and its derivatives [J].

Ottoni, O ;

Cruz, R ;

Alves, R .

TETRAHEDRON, 1998, 54 (46) :13915-13928

[5]

SETTIMO AD, 1965, TETRAHEDRON, V21, P1923

← 1 →