Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction.
25 Jun 2021-Journal of Organic Chemistry (American Chemical Society (ACS))-Vol. 86, Iss: 14, pp 9733-9743
TL;DR: In this article, a Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed to synthesize biologically active 1,8-dioxodecahydroacridine derivatives.
Abstract: A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.
Citations
More filters
TL;DR: A series of biologically important 2-amino-4H-chromenes functionalized with different substituents has been synthesized through one-pot multicomponent reaction catalysed by p-cymene Ru(II) organometallic complexes encompassing N˄O chelated carbazole based hydrazone ligands as discussed by the authors .
Abstract: A series of biologically important 2-amino-4H-chromenes functionalized with different substituents has been synthesized through one-pot multicomponent reaction catalysed by p-cymene Ru(II) organometallic complexes encompassing N˄O chelated carbazole based hydrazone ligands....
5 citations
TL;DR: In this paper, a convenient one-pot synthesis of heterocyclic nucleous acridine derivative compound has been achieved, where the mixture of dimedone, substituted benzaldehyde and aniline were catalyzed by efficient In2O3-SiO2 heterogeneous reusable catalyst in ethanol to obtain the desired acridines derivatives with good yield.
1 citations
TL;DR: Ruthenium-catalyzed multicomponent reactions (MCRs) as discussed by the authors is an unrivalled synthetic technique and is used by chemists at an accelerating rate in recent years.
Abstract:
In multicomponent reactions (MCRs), highly functionalized compounds can be formed through the reaction between three or more reactants in a one-pot manner. These reactions provide products through the utilization of a lesser amounts of energy, time, and effort. MCRs also possess advantages like the generation of lesser waste materials, fewer resources are needed, high convergence etc. In terms of energy economy and atom economy, MCRs are superior to multistep synthesis. A wide range of products can be acquired by combining the reagents in a variety of ways and thus MCRs became popular in various fields such as catalysis, pharmaceutical chemistry, material science, agrochemistry, fine chemistry and so on. MCRs obey the principles of green chemistry because these approaches are simple and eco-friendly. MCR is established as an unrivalled synthetic technique and is used by chemists at an accelerating rate in recent years. Ruthenium catalysts are cheap in comparison to palladium and rhodium, and generally show high activity. Ru possesses wide-ranging oxidation states due to its 4d75s1 electronic configuration. Numerous organic reactions are catalyzed by ruthenium and they are utilized in the formation of a wide range of pharmaceuticals and natural products, with biological importance. Minimum amounts of waste materials are formed in most of the ruthenium-catalyzed reactions and hence ruthenium catalysis pave way to environmentally benign protocols. Ruthenium chemistry has had a really big impact on organic synthesis in recent years that it is now on par with palladium in terms of relevance. The developments in the field of ruthenium-catalyzed multicomponent reactions are highlighted in this review, covering the literature up to 2021.
TL;DR: In this article , a series of unsymmetrical C-N linked bis heterocycles bearing quinazolinone and acridinedione skeletons have been synthesized in an acid promoted one pot multicomponent reaction.
Abstract: A novel series of unsymmetrical C-N linked bis heterocycles bearing quinazolinone and acridinedione skeletons have been synthesized in an acid promoted one pot multicomponent reaction. A blend of 6-aminoquinazolin-4-(3H)-one, aromatic aldehydes and cyclohexane-1,3-dione in a simple and efficient condensation-cyclization reaction using hydrochloric acid in catalytic amount as catalyst afforded unsymmetrical bis hybrids in good to excellent yields. Multiheterocyclic hybrid compounds were also synthesized using heterocyclic ring containing aldehyde in three component reaction. The synthesized quinazolinone-acridindione hybrids were characterized using spectroscopic techniques such as a IR, 1H NMR, 13C NMR, ESI-mass and HRMS.
TL;DR: In this article , an Fe-mediated four-component reaction of enaminones, anhydrides and tetrahydrofuran through a cascade [1 + 2 + 3]-cyclization/esterification process is presented.
Abstract: An Fe-mediated four-component reaction of enaminones, anhydrides and tetrahydrofuran through a cascade [1 + 2 + 3]-cyclization/esterification process is presented. This protocol provides a new and effective method to construct 4-alkylated 1,4-dihydropyridines with an ester fragment. Cyclic ether is employed as the C4 source of 1,4-dihydropyridines for the first time.
References
More filters
TL;DR: This paper presents a new approach to drug design called “combinatorial biosynthesis and drug discovery through nanofiltration”, which combines the efforts of a single investigator with those of a number of other scientists.
Abstract: Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, … 7, where most of the atoms of the starting materials are incorporated in the final product.1 Several descriptive tags are regularly attached to MCRs (Fig. 1): they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in one-step instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2 Therefore MCRs are often a useful alternative to sequential multistep synthesis.
Open in a separate window
Figure 1
Above: multistep syntheses can be divergent (sequential) or convergent; below: in analogy MCR reactions are convergent and one or two component reactions are divergent or less convergent.
1,840 citations
1,325 citations
TL;DR: Acceptorless dehydrogenation and related dehydrogenative coupling reactions have the potential for redirecting synthetic strategies to the use of sustainable resources, devoid of toxic reagents and deleterious side reactions, with no waste generation.
Abstract: Conventional oxidations of organic compounds formally transfer hydrogen atoms from the substrate to an acceptor molecule such as oxygen, a metal oxide, or a sacrificial olefin. In acceptorless dehydrogenation (AD) reactions, catalytic scission of C-H, N-H, and/or O-H bonds liberates hydrogen gas with no need for a stoichiometric oxidant, thereby providing efficient, nonpolluting activation of substrates. In addition, the hydrogen gas is valuable in itself as a high-energy, clean fuel. Here, we review AD reactions selectively catalyzed by transition metal complexes, as well as related transformations that rely on intermediates derived from reversible dehydrogenation. We delineate the methodologies evolving from this recent concept and highlight the effect of these reactions on chemical synthesis.
1,088 citations
TL;DR: An overview of general strategies that allow the design of novel multicomponent reactions is presented and the challenges and opportunities for the future are discussed.
Abstract: Multicomponent reactions have become increasingly popular as tools for the rapid generation of small-molecule libraries. However, to ensure sufficient molecular diversity and complexity, there is a continuous need for novel reactions. Although serendipity has always played an important role in the discovery of novel (multicomponent) reactions, rational design strategies have become much more important over the past decade. In this Review, we present an overview of general strategies that allow the design of novel multicomponent reactions. The challenges and opportunities for the future will be discussed.
1,036 citations
TL;DR: In this paper, the metal catalyst returned the hydrogen to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing CC bonds and β-functionalised alcohols.
Abstract: Alcohols can be temporarily converted into carbonyl compounds by the metal-catalysed removal of hydrogen. The carbonyl compounds are reactive in a wider range of transformations than the precursor alcohols and can react in situ to give imines, alkenes, and α-functionalised carbonyl compounds. The metal catalyst, which had borrowed the hydrogen, then returns it to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing CC bonds and β-functionalised alcohols.
929 citations