One-pot synthesis of 2-amino-3-cyanopyridine derivatives under solvent-free conditions

被引：24

作者：

Ghorbani-Vaghei, Ramin ^{[1
]}

Toghraei-Semiromi, Zahra ^{[1
]}

Karimi-Nami, Rahman ^{[2
]}

机构：

[1] Bu Ali Sina Univ, Dept Organ Chem, Fac Chem, Hamadan 65174, Iran

[2] Univ Tehran, Sch Chem, Univ Coll Sci, Tehran, Iran

来源：

COMPTES RENDUS CHIMIE | 2013年 / 16卷 / 12期

关键词：

2-Amino-3-cyanopyridine; Multicomponent reaction; Aldehyde; Ketone; Malononitrile; Ammonium acetate; Solvent-free; TBBDA; PBBS; MILD; N,N,N',N'-TETRABROMOBENZENE-1,3-DISULFONYLAMIDE; INHIBITORS; DISCOVERY; REAGENTS;

D O I：

10.1016/j.crci.2013.06.006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of 2-amino-3-cyanopyridines were obtained from aryl aldehydes, substituted acetophenones, malononitrile and ammonium acetate in good to excellent yields by proceeding through a simple, mild and efficient procedure utilizing N,N,N ',N '-tetra-bromobenzene-1,3-disulfonamide [TBBDA and poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) IPBBS] as catalysts. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：1111 / 1117

页数：7

共 22 条

[11] Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as efficient reagents for synthesis of quinolines [J].

Ghorbani-Vaghei, Ramin ;

Akbari-Dadamahaleh, Somayeh .

TETRAHEDRON LETTERS, 2009, 50 (09) :1055-1058

[12] Synthesis of novel 3-pyridinecarbonitriles with amino acid function and their fluorescence properties [J].

Girgis, AS ;

Kalmouch, A ;

Hosni, HM .

AMINO ACIDS, 2004, 26 (02) :139-146

[13]

KAMBE S, 1980, SYNTHESIS-STUTTGART, P366

[14] Particle-in-Cell Analysis of 1 MW/110 GHz Gyrotron Interaction Cavity [J].

Kumar, Nitin ;

Singh, Udaybir ;

Kumar, Anil ;

Singh, T. P. ;

Sinha, A. K. .

FREQUENZ, 2011, 65 (3-4) :65-72

[15] 2-amino-6-furan-2-yl-4-substituted nicotinonitriles as A2A adenosine receptor antagonists [J].

Mantri, Monica ;

de Graaf, Olivier ;

van Veldhoven, Jacobus ;

Goblyos, Aniko ;

von Frijtag, Jacobien K. ;

Kuenzel, Drabbe ;

Mulder-Krieger, Thea ;

Link, Regina ;

de Vries, Henk ;

Beukers, Margot W. ;

Brussee, Johannes ;

Ijzerman, Adriaan P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4449-4455

[16] Discovery of novel and selective IKK-β serine-threonine protein kinase inhibitors.: Part 1 [J].

Murata, T ;

Shimada, M ;

Sakakibara, S ;

Yoshino, T ;

Kadono, H ;

Masuda, T ;

Shimazaki, M ;

Shintani, T ;

Fuchikami, K ;

Sakai, K ;

Inbe, H ;

Takeshita, K ;

Niki, T ;

Umeda, M ;

Bacon, KB ;

Ziegelbauer, KB ;

Lowinger, TB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (05) :913-918

[17]

Roth H.J., 1988, DRUG SYNTHESIS, V1

[18] One-pot synthesis of 2-amino-3-cyanopyridine derivatives under microwave irradiation without solvent [J].

Shi, F ;

Tu, SJ ;

Fang, F ;

Li, TJ .

ARKIVOC, 2005, :137-142

[19] Recent progress in the application of N-halo reagents in the synthesis of heterocyclic compounds [J].

Veisi, Hojat ;

Ghorbani-Vaghei, Ramin .

TETRAHEDRON, 2010, 66 (38) :7445-7463

[20]

Vyas DH, 2009, INDIAN J CHEM B, V48, P833

← 1 2 3 →