Literature DB >> 26829937

Vanillic aldehydes for the one-pot synthesis of novel 2-oxo-1,2,3,4-tetrahydropyrimidines.

Jovana Muškinja1, Nenad Janković2, Zoran Ratković1, Goran Bogdanović3, Zorica Bugarčić1.   

Abstract

A small library of novel 2-oxo-1,2,3,4-tetrahydropyrimidines was synthesized via a one-pot multicomponent Biginelli reaction. Copper complex [Formula: see text] which was used for the first time as a homogeneous and heterogeneous catalyst, makes this a facile and efficient reaction at room temperature. All the obtained products fall out of the solution in pure form and are easily isolated via filtration in good-to-excellent yields. The molecular structure of one of the products, ethyl 6-methyl-2-oxo-4-(4[Formula: see text]-isopropoxy-3[Formula: see text]-methoxyphenyl) - 1,2,3,4 - tetrahydropyrimidine-5- carboxylate, has been determined by X-ray crystallography. All non-hydrogen atoms in the heterocyclic, six-membered ring are determined to be approximately coplanar.

Entities:  

Keywords:  Heterocycles; Heterogeneous catalysis; Homogeneous catalysis; Multicomponent reactions (MCRs)

Mesh:

Substances:

Year:  2016        PMID: 26829937     DOI: 10.1007/s11030-016-9658-y

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  12 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.

Authors:  Hung Yi Kristal Kaan; Venkatasubramanian Ulaganathan; Oliver Rath; Hana Prokopcová; Doris Dallinger; C Oliver Kappe; Frank Kozielski
Journal:  J Med Chem       Date:  2010-08-12       Impact factor: 7.446

Review 3.  Biologically active dihydropyrimidones of the Biginelli-type--a literature survey.

Authors:  C O Kappe
Journal:  Eur J Med Chem       Date:  2000-12       Impact factor: 6.514

4.  Water-tolerant and reusable Lewis acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions.

Authors:  Min Wang; Zhiguo Song; Heng Jiang; Hong Gong
Journal:  Prep Biochem Biotechnol       Date:  2010       Impact factor: 2.162

5.  Efficient conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-one to pyrimidines via PyBroP-mediated coupling.

Authors:  Fu-An Kang; Jason Kodah; Qunying Guan; Xiaobing Li; William V Murray
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

6.  Pyrimidine-core extended pi-systems: general synthesis and interesting fluorescent properties.

Authors:  Kenichiro Itami; Daisuke Yamazaki; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

7.  Design of 2,5-dimethyl-3-(6-dimethyl-4-methylpyridin-3-yl)-7-dipropylaminopyrazolo[1,5-a]pyrimidine (NBI 30775/R121919) and structure--activity relationships of a series of potent and orally active corticotropin-releasing factor receptor antagonists.

Authors:  Chen Chen; Keith M Wilcoxen; Charles Q Huang; Yun-Feng Xie; James R McCarthy; Thomas R Webb; Yun-Fei Zhu; John Saunders; Xin-Jun Liu; Ta-Kung Chen; Haig Bozigian; Dimitri E Grigoriadis
Journal:  J Med Chem       Date:  2004-09-09       Impact factor: 7.446

8.  Phosphonic acid functionalized ordered mesoporous material: a new and ecofriendly catalyst for one-pot multicomponent Biginelli reaction under solvent-free conditions.

Authors:  Malay Pramanik; Asim Bhaumik
Journal:  ACS Appl Mater Interfaces       Date:  2014-01-07       Impact factor: 9.229

9.  Biginelli reaction catalyzed by copper nanoparticles.

Authors:  Manika Dewan; Ajeet Kumar; Amit Saxena; Arnab De; Subho Mozumdar
Journal:  PLoS One       Date:  2012-08-17       Impact factor: 3.240

10.  Copper(II) sulfamate: an efficient catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones and thiones.

Authors:  Chen-Jiang Liu; Ji-De Wang
Journal:  Molecules       Date:  2009-02-13       Impact factor: 4.411

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  3 in total

1.  A new class of half-sandwich ruthenium complexes containing Biginelli hybrids: anticancer and anti-SARS-CoV-2 activities.

Authors:  Nenad Janković; Emilija Milović; Jelena Đorović Jovanović; Zoran Marković; Milan Vraneš; Tatjana Stanojković; Ivana Matić; Marija Đorđić Crnogorac; Olivera Klisurić; Miroslav Cvetinov; Syed Nasir Abbas Bukhari
Journal:  Chem Biol Interact       Date:  2022-06-22       Impact factor: 5.168

2.  Synthesis and Characterization of Dihydrouracil Analogs Utilizing Biginelli Hybrids.

Authors:  Syed Nasir Abbas Bukhari; Hasan Ejaz; Mervat A Elsherif; Nenad Janković
Journal:  Molecules       Date:  2022-05-04       Impact factor: 4.927

3.  Chitosan nanobeads loaded with Biginelli hybrids as cell-selective toxicity systems with a homogeneous distribution of the cell cycle in cancer treatment.

Authors:  Jovana Ristovski Trifunović; Željko Žižak; Smilja Marković; Nenad Janković; Nenad Ignjatović
Journal:  RSC Adv       Date:  2020-11-13       Impact factor: 4.036

  3 in total

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