The molecular diversity scope of 4-hydroxycoumarin in the synthesis of heterocyclic compounds via multicomponent reactions

Biginelli, an important multicomponent reaction provides an avenue for the synthesis of different biologically active heterocyclic compounds. During the past decade, one pot multicomponent reactions have attracted the attention of organic and medicinal chemists due to high atom economy, time and enery saving convergent nature. The present manuscript reports a simple one pot three component synthesis of 3, 4-dihydroprimidin-2(1H)-thiones from various diversely substituted aldehydes, ethyl acetoacetate and thiourea using a orange peel powder as a natural catalyst on ultrasonic irradiation in aqueous medium as the solvent. The advantages of this reaction are less reaction time, high yield, easy availability of the catalyst and green nature.

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Multicomponent Reactions

Molecules ◽

10.3390/molecules24132372 ◽

2019 ◽

Vol 24 (13) ◽

pp. 2372 ◽

Cited By ~ 5

Author(s):

Cristina Cimarelli

Keyword(s):

Multicomponent Reactions ◽

Molecular Diversity ◽

Special Issue ◽

Molecular Architectures

Multicomponent Reactions appear to be ideal for any form of synthesis, because of their numerous advantages in terms of sustainability and selectivity in building up complex molecular architectures, with high molecular diversity. This Special Issue collects seven contributions which expand our knowledge about Multicomponent Reactions, providing a good overview about innovative reactivities and applications.

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Palladium-mediated cascade or multicomponent reactions: A new route to carbo- and heterocyclic compounds

Pure and Applied Chemistry ◽

10.1351/pac200678020231 ◽

2006 ◽

Vol 78 (2) ◽

pp. 231-239 ◽

Cited By ~ 27

Author(s):

Geneviève Balme ◽

Didier Bouyssi ◽

Nuno Monteiro

Keyword(s):

Transition Metal ◽

Intramolecular Cyclization ◽

Heterocyclic Compounds ◽

Multicomponent Reactions ◽

Addition Reaction ◽

Carbon Bond ◽

Bond Forming ◽

Carbon Nucleophiles ◽

Carbon Carbon Bond

In recent years, new processes based on transition-metal-mediated intramolecular addition reaction of heteronucleophiles and stabilized carbon nucleophiles to unactivated alkenes and alkynes have been developed in our laboratory. In this article, we summarize a number of recent synthetic applications of these new processes. Emphasis is placed on the development of multicomponent reactions based on a Pd-mediated intramolecular cyclization coupled with a carbon-carbon bond-forming reaction. Applications of this methodology to the synthesis of natural lignans are also reported.

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Isocyanide and Meldrum's acid-based multicomponent reactions in diversity-oriented synthesis: from a serendipitous discovery towards valuable synthetic approaches

RSC Advances ◽

10.1039/c6ra11701e ◽

2016 ◽

Vol 6 (63) ◽

pp. 58142-58159 ◽

Cited By ~ 28

Author(s):

Ahmad Shaabani ◽

Seyyed Emad Hooshmand

Keyword(s):

Multicomponent Reactions ◽

Molecular Diversity ◽

Single Step ◽

Atom Economy ◽

Meldrum's Acid ◽

Meldrum’S Acid ◽

Diversity Oriented Synthesis ◽

Synthetic Approaches

Multicomponent reactions, which lead to synthesis of target compounds with inherent molecular diversity, greater efficiency and atom economy, are single step types of reactions made from three or more reactants attract the attention of all chemists.

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Hydroalkylation leading to heterocyclic compounds (Part 2): practical synthesis of polysubstituted 1,2,3,4-tetrahydropyridines through multicomponent reactions (MCRs)

Tetrahedron ◽

10.1016/j.tet.2009.07.046 ◽

2009 ◽

Vol 65 (38) ◽

pp. 7985-7988 ◽

Cited By ~ 25

Author(s):

Wei-Bing Liu ◽

Huan-Feng Jiang ◽

Shi-Fa Zhu ◽

Wei Wang

Keyword(s):

Heterocyclic Compounds ◽

Multicomponent Reactions ◽

Practical Synthesis

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Dimroth´s Rearrangement as a Synthetic Strategy Towards New Heterocyclic Compounds

Current Organic Chemistry ◽

10.2174/1385272824999200805114837 ◽

2020 ◽

Vol 24 (17) ◽

pp. 1999-2018

Author(s):

Vitor F. Ferreira ◽

Thais de B. da Silva ◽

Fernanda P. Pauli ◽

Patricia G. Ferreira ◽

Luana da S. M. Forezi ◽

...

Keyword(s):

Bioactive Compounds ◽

Heterocyclic Compounds ◽

Large Scale ◽

Molecular Diversity ◽

Biologically Active ◽

Scale Production ◽

Dimroth Rearrangement ◽

Synthetic Strategy ◽

Large Scale Production ◽

Synthetic Approaches

Molecular rearrangements are important tools to increase the molecular diversity of new bioactive compounds, especially in the class of heterocycles. This review deals specifically with a very famous and widely applicable rearrangement known as the Dimroth Rearrangement. Although it has originally been observed for 1,2,3-triazoles, its amplitude was greatly expanded to other heterocycles, as well as from laboratory to large scale production of drugs and intermediates. The reactions that were discussed in this review were selected with the aim of demonstrating the windows that may be open by the Dimroth's rearrangement, especially in what regards the development of new synthetic approaches toward biologically active compounds.

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Recent Advances in C-C/Heteroatom Bond Forming and Annulation Reactions of β-Ketodithioesters

Current Organic Synthesis ◽

10.2174/1570179418666210614142939 ◽

2021 ◽

Vol 18 ◽

Author(s):

Laishram Momota Devi ◽

Thokchom Prasanta Singh ◽

Okram Mukherjee Singh

Keyword(s):

Heterocyclic Compounds ◽

Multicomponent Reactions ◽

Building Blocks ◽

Heterocyclic Synthesis ◽

Bond Forming ◽

Mild Conditions ◽

The Past ◽

Rapid Construction ◽

Fresh Perspective ◽

Good Number

: β Ketodithioesters (KDEs) are versatile building blocks for the rapid construction of various heterocyclic compounds. Quite a good number of successful reactions based on KDEs have been developed in the past decade for the construction of heterocyclic skeletons under mild conditions. This review covers the new C-C/X bond formation and annulation reactions of KDEs with dielectrophilic or dinucleophilic reagents. Multicomponent reactions using KDEs to construct various heterocycles are also the major contents in this review. Objective: The aim of this review is to bring a fresh perspective on the application of KDEs in organic synthesis covering from 2013 to 2020. Conclusion: From this review, it is clear that KDEs have been the object of numerous studies on its use in heterocyclic synthesis. The presence of different functional groups on this synthon permits the incorporation of C-C/X sources into the final targets, which is the beauty of KDEs.

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Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.121 ◽

2016 ◽

Vol 12 ◽

pp. 1269-1301 ◽

Cited By ~ 82

Author(s):

Mohammad Haji

Keyword(s):

Organic Compounds ◽

Heterocyclic Compounds ◽

Multicomponent Reactions ◽

Synthetic Chemistry ◽

Phosphonate Group ◽

Wide Range ◽

Efficient Route ◽

Organophosphorus Chemistry

Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

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