One-Pot Four-Component Synthesis of Thieno[2,3-d]pyrimidin-4-amines via Sequential Gewald/Cyclocondensation Reactions

被引：13

作者：

Adib, Mehdi ^{[1
]}

Janatian Ghazvini, Helia ^{[1
]}

Soheilizad, Mehdi ^{[1
]}

Saeedi, Sara ^{[1
]}

Tajbakhsh, Mahmood ^{[2
]}

Amanlou, Massoud ^{[3
,4
]}

机构：

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

[2] Mazandaran Univ, Dept Organ Chem, Fac Chem, Babol Sar, Iran

[3] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Tehran, Iran

[4] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran, Iran

来源：

HELVETICA CHIMICA ACTA | 2015年 / 98卷 / 08期

关键词：

Thieno[2; 3-d]pyrimidin-4-amines; Gewald; cyclocondensation reactions; Multicomponent reactions (MCRs); Solvent-free synthesis; MULTICOMPONENT REACTIONS; ACIDIC CONDITIONS; DERIVATIVES; NITRILES;

D O I：

10.1002/hlca.201500008

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

A one-pot four-component synthesis of thieno[2,3-d]pyrimidin-4-amines via sequential Gewald/cyclocondensation reactions is described. 2-Aminothiophene-3-carbonitriles obtained from the Gewald reaction between cyclic ketones, malononitrile, and sulfur underwent a condensationcyclization reaction with benzonitriles under solvent-free conditions to afford the title compounds in excellent yields.

引用

收藏

页码：1079 / 1086

页数：8

相关论文

共 34 条

[1]

Microwave-assisted reaction between 2-aminobenzoic acids, 2-hydroxybenzaldehydes, and arylboronic acids: a one-pot three-component synthesis of bridgehead bicyclo[4.4.0]boron heterocycles [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Bijanzadeh, Hamid Reza ;

Zhu, Long-Guan .

TETRAHEDRON, 2012, 68 (16) :3377-3383

[2]

Synthesis, analgesic, anti-inflammatory, ulcerogenic index and antibacterial activities of novel 2-methylthio-3-substituted-5,6,7,8-tetrahydrobenzo(b)thieno[2,3-d]pyrimidin-4(3H)-ones [J].

Alagarsamy, V. ;

Meena, S. ;

Ramseshu, K. V. ;

Solomon, V. R. ;

Thirumurugan, K. ;

Dhanabal, K. ;

Murugan, M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (11) :1293-1300

[3]

[Anonymous], 1996, ADV HETEROCYCL CHEM

[4]

Bhuiyan Md. Mosharef Hossain, 2006, Acta Pharmaceutica (Zagreb), V56, P441

[5]

Brewster W., 2007, Patent, Patent No. [WO 2007046809, 2007046809]

[6]

Substituted 2-Aminothiopen-derivatives: A potential new class of GluR6-Antagonists [J].

Briel, D. ;

Rybak, A. ;

Kronbach, C. ;

Unverferth, K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :69-77

[7]

Microwave-Assisted Synthesis of 4-Amino-2-arylthieno[2,3-d]pyrimidines and Their Subsequent Functionalization [J].

Chen, Binbin ;

Perspicace, Enrico ;

Hesse, Stephanie ;

Kirsch, Gilbert .

SYNTHESIS-STUTTGART, 2010, (14) :2413-2418

[8]

Heterocycles derived from heteroatom-substituted carbenes [J].

Cheng, Y ;

Meth-Cohn, O .

CHEMICAL REVIEWS, 2004, 104 (05) :2507-2530

[9]

Novel, highly potent adenosine deaminase inhibitors containing the pyrazolo[3,4-d]pyrimidine ring system.: Synthesis, structure-activity relationships, and molecular modeling studies [J].

Da Settimo, F ;

Primofiore, G ;

La Motta, C ;

Taliani, S ;

Simorini, F ;

Marini, AM ;

Mugnaini, L ;

Lavecchia, A ;

Novellino, E ;

Tuscano, D ;

Martini, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (16) :5162-5174

[10]

REACTION OF NITRILES UNDER ACIDIC CONDITIONS .1. A GENERAL-METHOD OF SYNTHESIS OF CONDENSED PYRIMIDINES [J].

DAVE, KG ;

SHISHOO, CJ ;

DEVANI, MB ;

KALYANARAMAN, R ;

ANANTHAN, S ;

ULLAS, GV ;

BHADTI, VS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (07) :1497-1500

← 1 2 3 4 →