Synthesis of 2-substituted-7-azaindoles from 2-amino-3-picolin

被引：11

作者：

Parcerisa, Javier ^{[1
]}

Romero, Manel ^{[1
]}

Dolors Pujol, Maria ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Unitat Associada CSIC, Quim Farmaceut Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 03期

关键词：

D O I：

10.1016/j.tet.2007.11.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy route to the synthesis of 2-substituted-7-azaindole derivatives has been developed. The carbinol intermediate dissolved in DMF undergoes cyclization upon treatment with sodium hydride, trifluoroacetic anhydride, and trifluoroacetic acid at 120 degrees C in a straightforward and one-pot step. An alternative methodology using (CF3SO2)(2)O in acetonitrile in basic media followed by the addition of CF3COOH affords the expected 2-substituted azaindole in best yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：500 / 507

页数：8

共 50 条

[21] A NEW ENTRY FOR PREPARATION OF 2-SUBSTITUTED AZAINDOLES
Shaykoon, Montaser
Shaykoon, Ahmed
Inagaki, Fuyuhiko
Mukai, Chisato
HETEROCYCLES, 2010, 80 (01) : 133 - 139
[22] 2-phenyl-3-pyridinyl substituted 7-azaindoles as inhibitors of mitogen-activated protein kinase
不详
EXPERT OPINION ON THERAPEUTIC PATENTS, 1998, 8 (11) : 1517 - 1523
[23] Efficient One-Pot Synthesis of 3-Amino-7-azaindoles Under Microwave Irradiation
Yang, Hai-Kui
You, Wen-Wei
Yan, Guang-Hua
Jiang, Zhi-Hong
Zhao, Pei-Liang
Zhou, Zhong-Zhen
SYNTHETIC COMMUNICATIONS, 2014, 44 (08) : 1165 - 1171
[24] DERIVATIVES OF AZAINDOLES .40. SYNTHESIS OF 3-METHYL-5-AZAINDOLES AND 2,3-DIMETHYL-5-AZAINDOLES
MARSHALKIN, MF
YAKHONTO.LN
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1972, (05): : 652 - +
[25] The Fischer Reaction in the Synthesis of 2,3-Disubstituted 7-Azaindoles*
R. S. Alekseyev
S. R. Amirova
E. V. Kabanova
V. I. Terenin
Chemistry of Heterocyclic Compounds, 2014, 50 : 1305 - 1315
[26] Synthesis of 2,5-Disubstituted 6-Azaindoles from Substituted Aziridines via Intramolecular Cyclization
Lee, Hogyu
Kim, Jun Hee
Lee, Won Koo
Jung, Jae-Hoon
Ha, Hyun-Joon
ORGANIC LETTERS, 2012, 14 (12) : 3120 - 3122
[27] The Fischer Reaction in the Synthesis of 2,3-Disubstituted 7-Azaindoles
Alekseyev, R. S.
Amirova, S. R.
Kabanova, E. V.
Terenin, V. I.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (09) : 1305 - 1315
[28] PHOTOCHEMISTRY OF 3-AMINO-2-ALKENIMINES - SYNTHESIS OF SUBSTITUTED QUINOLINES
CAMPOS, PJ
TAN, CQ
GONZALEZ, JM
RODRIGUEZ, MA
TETRAHEDRON LETTERS, 1993, 34 (33) : 5321 - 5324
[29] SYNTHESIS OF SUBSTITUTED 2-AMINO-3-(ALKYL OR ARYL)SULFONYLPYRROLES
MATTSON, RJ
WANG, LC
SOWELL, JW
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (08) : 1793 - 1795
[30] SYNTHESIS AND PROPERTIES OF SUBSTITUTED 3-AMINO-2H-AZIRINES
EREMEYEV, AV
PISKUNOVA, IP
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (07): : 867 - 887

← 1 2 3 4 5 →