Versatility of the Biginelli reaction: Synthesis of new biphenyl dihydropyrimidin-2-thiones using different ketones as building blocks

被引：18

作者：

Goncalves, Itamar Luis ^{[1
]}

Davi, Leonardo ^{[1
]}

Rockenbach, Liliana ^{[1
]}

das Neves, Gustavo Machado ^{[1
]}

Kagami, Luciano Porto ^{[1
]}

Santos Canto, Romulo Faria ^{[3
]}

Figueiro, Fabricio ^{[2
]}

Oliveira Battastini, Ana Maria ^{[2
]}

Eifler-Lima, Vera Lucia ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Fac Farm, Lab Sintese Organ Med LaSOM, Ave Ipiranga 2752, Porto Alegre, RS, Brazil

[2] Univ Fed Rio Grande do Sul, Lab 22, Dept Bioquim, Porto Alegre, RS, Brazil

[3] Univ Fed Ciencias Saude Porto Alegre, Programa Posgrad Ciencias Saude, Lab Quim Med Compostos Selenio QMCSe, Rua Sarmento Leite,245 Ctr Hist, Porto Alegre, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 28期

关键词：

Biginelli reaction; Structural diversity; Multicomponent reaction;

D O I：

10.1016/j.tetlet.2018.06.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A multi-component synthesis of biphenyl dihydropyrimidin-2-thiones from 1-phenylthiourea, aldehydes and ketones or di-ketones has been demonstrated. The reaction proceeded well for aldehydes with electron donor or acceptor substituents under mild conditions. (C) 2018 Published by Elsevier Ltd.

引用

页码：2759 / 2762

页数：4

共 14 条

[1] A mini-review on Biginelli adducts with notable pharmacological properties [J].

de Fatima, Angelo ;

Braga, Taniris C. ;

Neto, Leonardo da S. ;

Terra, Bruna S. ;

Oliveira, Breno G. F. ;

da Silva, Daniel L. ;

Modolo, Luzia V. .

JOURNAL OF ADVANCED RESEARCH, 2015, 6 (03) :363-373

[2] Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines [J].

Goncalves, Itamar Luis ;

Rockenbach, Liliana ;

das Neves, Gustavo Machado ;

Goethel, Gabriela ;

Nascimento, Fabiana ;

Kagami, Luciano Porto ;

Figueiro, Fabricio ;

de Azambuja, Gabriel Oliveira ;

Dias, Amanda de Fraga ;

Amaro, Andressa ;

de Souza, Lauro Mera ;

Pitta, Ivan da Rocha ;

Avila, Daiana Silva ;

Kawano, Daniel Fabio ;

Garcia, Solange Cristina ;

Oliveira Battastinic, Ana Maria ;

Eifler-Lima, Vera Lucia .

MEDCHEMCOMM, 2018, 9 (06) :995-1010

[3] Thioureas as Building Blocks for the Generation of Heterocycles and Compounds with Pharmacological Activity: An Overview [J].

Goncalves, Itamar Luis ;

de Azambuja, Gabriel Oliveira ;

Kawano, Daniel Fabio ;

Eifler-Lima, Vera Lucia .

MINI-REVIEWS IN ORGANIC CHEMISTRY, 2018, 15 (01) :28-35

[4] Bioisosteric approach in designing new monastrol derivatives: An investigation on their ADMET prediction using in silico derived parameters [J].

Hassan, Syed Fahad ;

Rashid, Umer ;

Ansari, Farzana Latif ;

Ul-Haq, Zaheer .

JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2013, 45 :202-210

[5] PEG-SANM nanocomposite: a new catalytic application towards clean and highly efficient Biginelli-like reaction under solvent-free conditions [J].

Heirati, Seyedeh Zahra Dalil ;

Shirini, Farhad ;

Shojaei, Abdollah Fallah .

RSC ADVANCES, 2016, 6 (71) :67072-67085

[6] Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review [J].

Kaur, Ramandeep ;

Chaudhary, Sandeep ;

Kumar, Kapil ;

Gupta, Manish K. ;

Rawal, Ravindra K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 132 :108-134

[7] Biginelli reaction: an overview [J].

Nagarajaiah, Honnappa ;

Mukhopadhyay, Arindam ;

Moorthy, Jarugu Narasimha .

TETRAHEDRON LETTERS, 2016, 57 (47) :5135-5149

[8] Protecting Group Free Synthesis of Carboxyl-substituted Dihydropyrimidines Through Biginelli Reaction [J].

Ostapchuk, Eugeniy N. ;

Plaskon, Andrey S. ;

Grygorenko, Oleksandr O. ;

Tolmachev, Andrey A. ;

Ryabukhin, Sergey V. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (06) :1299-1303

[9] Regioselective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones: Screening of their biological activities against Ca2+-ATPase [J].

Putatunda, Salil ;

Chakraborty, Srabasti ;

Ghosh, Swatilekha ;

Nandi, Pinki ;

Chakraborty, Supriya ;

Sen, Parimal C. ;

Chakraborty, Arijit .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :223-231

[10] N-substituted ureas and thioureas in Biginelli reaction promoted by chlorotrimethylsilane:: Convenient synthesis of N1-alkyl-, N1-aryl-, and N1,N3-dialkyl-3,4-dihydropyrimidin-2(1H)-(thi)ones [J].

Ryabukhin, Sergey V. ;

Plaskon, Andrey S. ;

Ostapchuk, Eugeniy N. ;

Volochnyuk, Dmitriy M. ;

Tolmachev, Andrey A. .

SYNTHESIS-STUTTGART, 2007, (03) :417-427

← 1 2 →