Application of (2Z)-3-dimethylamino-2-(1H-indole-3-carbonyl) acrylonitrile in the synthesis of novel 3-heteroarylindoles: condensed meridianine analogs

被引：23

作者：

Radwan, Mohamed A. A. ^{[1
]}

Ragab, Eman A. ^{[2
]}

Shaaban, Mohamed R. ^{[2
]}

El-Nezhawy, Ahmed O. H. ^{[3
]}

机构：

[1] Natl Res Ctr, Appl Organ Chem Dept, Cairo, Egypt

[2] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt

[3] Natl Res Ctr, Chem Nat & Microbial Prod Dept, Cairo, Egypt

来源：

ARKIVOC | 2009年

关键词：

Indole; alkaloids; enaminonitrile; meridianines; natural products; X-ray; WATER MARINE SPONGE; INDOLE ALKALOIDS; A-D; DERIVATIVES; INDOLYLPYRIMIDINES; ANTIFUNGAL; TOPSENTIN; ACID;

D O I：

10.3998/ark.5550190.0010.727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Dimethylamino-2-(1H-indole-3-carbonyl)acrylonitrile (2) was treated with phenylhydrazine, in refluxing basic ethanol, afforded a single product N-1 or N-2 substituted pyrazole. Basic promoted cyclization of enaminonitrile 2 with alpha-heteroarylamines as N,N-1,3-dinucleophiles, condensed indolylpyrimidines as a new class of meridianine natural product analogs were obtained in moderate to good yields.

引用

页码：281 / 291

页数：11

共 47 条

[1]

Al-Zaydi K. M., 2000, J CHEM RES S, V13, P173

[2] Microwave assisted synthesis, part 1: Rapid solventless synthesis of 3-substituted coumarins and benzocoumarins by microwave irradiation of the corresponding enaminones [J].

Al-Zaydi, KM .

MOLECULES, 2003, 8 (07) :541-555

[3]

Allen G.R., 1973, Org. React, V20, P337

[4]

ALVAREZ M, 1991, HETEROCYCLES, V32, P1391

[5] SYNTHESIS AND ANTIINFLAMMATORY ACTIVITY OF INDOLYLACRYLIC AND METHYLACRYLIC ACIDS [J].

ANDREANI, A ;

RAMBALDI, M ;

LOCATELLI, A ;

PIFFERI, G .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (11) :903-906

[6] TOPSENTINS, NEW TOXIC BIS-INDOLE ALKALOIDS FROM THE MARINE SPONGE TOPSENTIA-GENITRIX [J].

BARTIK, K ;

BRAEKMAN, JC ;

DALOZE, D ;

STOLLER, C ;

HUYSECOM, J ;

VANDEVYVER, G ;

OTTINGER, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2118-2121

[7] Alboinon, an oxadiazinone alkaloid from the ascidian Dendrodoa grossularia [J].

Bergmann, T ;

Schories, D ;

Steffan, B .

TETRAHEDRON, 1997, 53 (06) :2055-2060

[8] Dragmacidins:: New protein phosphatase inhibitors from a southern Australian deep-water marine sponge, Spongosorites sp. [J].

Capon, RJ ;

Rooney, F ;

Murray, LM ;

Collins, E ;

Sim, ATR ;

Rostas, JAP ;

Butler, MS ;

Carroll, AR .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :660-662

[9] Reaction of methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with ureas:: facile entry into the polycyclic meridianin analogues with uracil structural unit [J].

Casar, Z ;

Bevk, D ;

Svete, J ;

Stanovnik, B .

TETRAHEDRON, 2005, 61 (31) :7508-7519

[10]

DANDIA A, 1993, INDIAN J CHEM B, V32, P1288

← 1 2 3 4 5 →