scholarly journals Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonic Acids in DMSO

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6839
Author(s):  
Yuliya E. Ryzhkova ◽  
Michail N. Elinson ◽  
Oleg I. Maslov ◽  
Artem N. Fakhrutdinov
Keyword(s):  
Reaction Mechanism ◽  
Organic Synthesis ◽  
Multicomponent Reactions ◽  
Room Temperature ◽  
Low Cost ◽  
2D Nmr ◽  
Biologically Active ◽  
Multicomponent Synthesis ◽  
2D Nmr Spectroscopy ◽  
Low Toxicity

Dimethyl sulfoxide is a widely used solvent in organic synthesis and in the pharmaceutical industry because of its low cost, stability, and low toxicity. Multicomponent reactions are an advanced approach that has become an efficient, economical, and eco-friendly substitute for the conventional sequential multi-step synthesis of various biologically active compounds. This approach was adopted for the synthesis of previously unknown 2-(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonic acids via transformation of salicylaldehydes, malononitrile dimer, and malonic acid. It was shown that the use of DMSO at room temperature makes it possible to synthesize previously unavailable compounds. The investigation of the reaction mechanism using 1H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized 5H-chromeno[2,3-b]pyridines was confirmed by 2D-NMR spectroscopy.

scholarly journals Multicomponent Synthesis of Dimethyl 2-(2,4-Diamino-3- cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate

Molbank ◽  
10.3390/m1308 ◽  
2021 ◽  
Vol 2022 (1) ◽  
pp. M1308
Author(s):  
Yuliya E. Ryzhkova ◽  
Oleg I. Maslov ◽  
Michail N. Elinson
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Infrared Spectroscopy ◽  
Magnetic Resonance ◽  
Organic Synthesis ◽  
Multicomponent Reactions ◽  
Room Temperature ◽  
Low Cost ◽  
Multicomponent Synthesis ◽  
Dimethyl Malonate ◽  
Efficient Construction

Dimethyl sulfoxide (DMSO) is widely used as a solvent in organic synthesis and in pharmacology because of its low cost, stability, and non-toxicity. Multicomponent reactions are a powerful synthetic tool for the rapid and efficient construction of complicated molecular frameworks. In this communication, the multicomponent transformation of salicylaldehyde, malononitrile dimer, and dimethyl malonate in DMSO at room temperature was carefully investigated to give dimethyl 2-(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate with good yield. The structure of the new compound was established by means of elemental analysis and mass, nuclear magnetic resonance, and infrared spectroscopy.

The double and triple role of L-(+)-tartaric acid and dimethyl urea: A prevailing green approach in organic synthesis

2021 ◽  
Vol 25 ◽  
Author(s):  
Rashid Ali ◽  
Ajay Kumar Chinnam ◽  
Vikas R. Aswar
Keyword(s):  
Tartaric Acid ◽  
Organic Synthesis ◽  
Low Cost ◽  
Organic Transformations ◽  
Green Approach ◽  
Dimethyl Urea ◽  
Low Toxicity ◽  
The One ◽  
Near Future

: The deep eutectic mixtures (DESs), introduced as novel alternative to usual volatile organic solvents for organic transformations has attracted a tremendous attention of the research community because of their low cost, negligible vapour pressure, low toxicity, biodegradability, recyclability, insensitive towards moisture, and readily availability from bulk renewable resources. Although, the low melting mixture of dimethyl urea (DMU)/L-(+)-tartaric acid (TA) is still infancy yet much effective as it play double and triple roles such as solvent, catalyst and/or reagent in a same pot for many crucial organic transformations. These unique properties of DMU/TA mixture prompted us to provide a quick overview of where the field stands presently, and where it might be going in near future. To our best knowledge, no review dealing with the applications of a low melting mixture of DMU/TA appeared in the literature except the one published in 2017 describing only the chemistry of indole systems. Therefore, we intended to reveal the developments of this versatile low melting mixture in the modern organic synthesis since its first report in 2011 by Köenig’s team to till date. Hopefully, the present review article will be useful to the researcher working not only in the arena of synthetic organic chemistry but also to the scientists working in other branches of science and technology.

‘On-water’ organic synthesis: a green, highly efficient, low cost and reusable catalyst system for biaryl synthesis under aerobic conditions at room temperature

RSC Advances ◽  
2015 ◽  
Vol 5 (63) ◽  
pp. 50655-50659 ◽  
Author(s):  
Bishwajit Saikia ◽  
Preeti Rekha Boruah ◽  
Abdul Aziz Ali ◽  
Diganta Sarma
Keyword(s):  
Organic Synthesis ◽  
Room Temperature ◽  
Low Cost ◽  
Suzuki Reaction ◽  
Catalyst System ◽  
Reusable Catalyst ◽  
Wide Range ◽  
Biaryl Synthesis ◽  
Phenylboronic Acids ◽  
Operational Simplicity

The PdCl2/sucrose/K2CO3/H2O system showed the superb catalytic activity towards the Suzuki reaction of a wide range of aryl/heteroaryl halides with diverse phenylboronic acids at room temperature with operational simplicity and shorter reaction time.

scholarly journals An Approach in Synthesis of 1-Morpholino-2-phenylethane-1,2-dione Catalyzed by Copper (II) Bromide

2020 ◽  
Vol 3 (3) ◽  
pp. 145
Author(s):  
Didin Mujahidin ◽  
Wiwin Mujiati ◽  
Anita Alni
Keyword(s):  
Room Temperature ◽  
Spectroscopic Method ◽  
2D Nmr ◽  
Biologically Active ◽  
Catalyst Loading ◽  
1H And 13C Nmr ◽  
Novel Approach ◽  
Acetophenone Derivatives ◽  
Simple Alternative ◽  
Acetyl Group

A novel approach towards synthesis of α-Ketoamides was serendipitously found in acetophenone's reaction with a secondary amine catalyzed by copper (II) bromide. This methodology is a promising simple alternative to access biologically active compounds containing α-Ketoamides. Reactions were carried out at room temperature using dimethyl sulfoxide (DMSO) as solvent and catalyst loading at 10 mol %. The products were purified using a chromatographic method and analyzed extensively by spectroscopic methods, namely 1D (1H and 13C) and 2D NMR (HMBC and HSQC). The reaction of acetophenone and morpholine furnished a yield of 6%. Acetophenone derivatives bearing benzyl and acetyl groups were prepared from para-hydroxy acetophenone with 25% and 99% yields, respectively. The products were analyzed by spectroscopic method, namely 1H and 13C NMR.  The presence of substituents, namely hydroxyl, benzyl, acetyl group, prevent the formation of α-Ketoamides. Formation of α-Ketoamides in this reaction condition was proposed as the result of the oxidation product in the catalytic cycle of Cu (II).

The Catalytic Activity of TiO2 Toward a Multicomponent Reaction Depends on its Morphology, Mechanoactivation and Presence of Visible Light

2020 ◽  
Vol 1 (1) ◽  
pp. 37-42
Author(s):  
Subramanian Thirumeni ◽  
Choumini Balasanthiran ◽  
Grigoriy Sereda
Keyword(s):  
Catalytic Activity ◽  
Visible Light ◽  
Tio2 Nanoparticles ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Room Temperature ◽  
Light Condition ◽  
Ambient Light ◽  
Multicomponent Synthesis ◽  
Ambient Light Condition

Aims: Test the hypothesis that the catalytic activity of TiO2 nanoparticles towards a liquidphase or mechanoactivated multicomponent reaction can be tuned by visible light and the shape of nanoparticles. Background: Catalytic multicomponent reactions have been proven to be excellent synthetic approaches to a series of biologically relevant compounds including 2-amino-4H-benzo[b]pyrans. However, the potential photocatalytic activity and structural diversity of nanostructured catalysts remained underutilized in the design of new catalytic systems. Objective: Harness the photocatalytic potential and diverse morphology of TiO2 particles as catalysts for the liquid phase and mechanoactivated multicomponent organic reactions. Results: Catalytic activity of TiO2 nanoparticles towards multicomponent synthesis of 2-amino-4Hbenzo[ b]pyrans is increased by visible light. The nanorod-shaped TiO2 nanoparticles have shown substantially higher catalytic activity towards mechanoactivated multicomponent synthesis of 2- amino-4H-benzo[b]pyrans than their spherically-shaped counterparts. Conclusion: : An efficient methodology for the synthesis of 2-amino-4H-benzo[b]pyrans under ambient light condition has been developed using TiO2 nanorods (high aspect ratio anatase nanocrystals) as photocatalyst. This simple method furnished the corresponding terahydrobenzopyrans in high yields via three component reaction of aldehyde, malononitrile, and dimidone under solvent free reaction conditions at room temperature. The reaction takes 8-10 min at room temperature under ambient light condition and the catalyst can be reused multiple times. Utilization of light and the nanorod morphology of the catalyst through mechanoactivation has been applied for the -first time to the synthetic technique of multicomponent reactions. The synthetic procedures for 2-amino-4Hbenzo[ b]pyrans have been improved.

scholarly journals Gold Catalyzed Multicomponent Reactions beyond A3 Coupling

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2255 ◽  
Author(s):  
Renso Visbal ◽  
Sara Graus ◽  
Raquel P. Herrera ◽  
M. Concepción Gimeno
Keyword(s):  
Organic Synthesis ◽  
Multicomponent Reactions ◽  
Molecular Diversity ◽  
Biologically Active ◽  
Active Compounds ◽  
The Past ◽  
New Methods ◽  
Complex Architectures ◽  
Interesting Approach ◽  
A3 Coupling

The preparation of complex architectures has inspired the search for new methods and new processes in organic synthesis. Multicomponent reactions have become an interesting approach to achieve such molecular diversity and complexity. This review intends to illustrate important gold-catalyzed examples for the past ten years leading to interesting skeletons involved in biologically active compounds.

scholarly journals Di-And Tri-Hydroxylated Kaurane Derivatives From Microbial Transformation Of Ent-Kaur-16-En-19-Ol By Cephalosporium Aphidicola And Their Allelopathic Activity On Lactuca Sativa (Lettuce)

2018 ◽  
Vol 34 (1) ◽  
pp. 57
Author(s):  
Diana Rocha ◽  
Jacqueline Aparecida Takahashi ◽  
Maria Amelia Diamantino Boaventura
Keyword(s):  
Organic Compounds ◽  
Organic Synthesis ◽  
Lactuca Sativa ◽  
Organic Molecules ◽  
Microbial Transformation ◽  
2D Nmr ◽  
Biologically Active ◽  
Chemical Modifications ◽  
Nmr Studies ◽  
Active Substances

The use of microorganisms to induce chemical modifications in organic molecules is a very useful tool in organic synthesis, to obtain biologically active substances. The fungus Cephalosporium aphidicola is known by its ability to hydroxylate several skeleton positions of many classes of organic compounds. In this work, the microbial transformation of ent-kaur-16-en-19-ol (1) by C. aphidicola, afforded two hydroxylated compounds, ent-kauran-16b,19-diol (2) and ent-kauran-16b,17,19-triol (3). Their structures were established by 1D and 2D-NMR studies. Both compounds were tested for their action on the growth of radical and shoot of Lactuca sativa.

scholarly journals The Isolation of Biologically Active Secondary Metabolites from New Zealand Marine Organisms

2021 ◽  
Author(s):  
◽  
Robert Alexander Keyzers
Keyword(s):  
New Zealand ◽  
2D Nmr ◽  
Structural Features ◽  
Marine Sponges ◽  
Biologically Active ◽  
The Novel ◽  
2D Nmr Spectroscopy ◽  
Naturally Occurring ◽  
Anti Inflammatory ◽  
Toxic Algal Bloom

<p>An improved protocol for the screening of marine sponges using cyclic loading, PSDVB, and both 1D and 2D NMR spectroscopy is described. Using this new methodology, 51 sponges were screened. Further investigations were carried out on seven of the 51 organisms, resulting in the isolation of several known and eight novel compounds. Clathriols A (32) and B (33) are novel sterols isolated from the sponge Clathria lissosclera. Both 32 and 33 possess the rare 14 Beta stereochemistry, a feature only naturally occurring in marine sponges. Both are also moderate anti-inflammatory compounds. Ten spongian diterpenes were isolated from the New Zealand, sponge Chelonaplysilla violacea, six of which are novel. Cadlinolides C (138) and D (139) are similar to several previously reported compounds while pourewic acid A (140), 15-methoxypourewic acid B (141), methylpourewate B (142) and pourewanone (143) have unique structural features and are of biogenetic significance. Pourewanone (143) is the first example of a formate isolated from the marine environment. Several of the novel diterpenes exhibit moderate anti-inflammatory activity. A potent dinoflagellate toxin was partially purified from cultures of the producing organism, Karenia brevisulcata. K. brevisulcata is a new dinoflagellate species implicated in a large toxic algal bloom in Wellington Harbour, New Zealand, which formed during the summer of 1997/1998. Although the toxin could not be identified, some of the functionality present, and several possible substructures, is proposed. The biological activity of the toxin is also described.</p>

scholarly journals The Isolation of Biologically Active Secondary Metabolites from New Zealand Marine Organisms

2021 ◽  
Author(s):  
◽  
Robert Alexander Keyzers
Keyword(s):  
New Zealand ◽  
2D Nmr ◽  
Structural Features ◽  
Marine Sponges ◽  
Biologically Active ◽  
The Novel ◽  
2D Nmr Spectroscopy ◽  
Naturally Occurring ◽  
Anti Inflammatory ◽  
Toxic Algal Bloom

<p>An improved protocol for the screening of marine sponges using cyclic loading, PSDVB, and both 1D and 2D NMR spectroscopy is described. Using this new methodology, 51 sponges were screened. Further investigations were carried out on seven of the 51 organisms, resulting in the isolation of several known and eight novel compounds. Clathriols A (32) and B (33) are novel sterols isolated from the sponge Clathria lissosclera. Both 32 and 33 possess the rare 14 Beta stereochemistry, a feature only naturally occurring in marine sponges. Both are also moderate anti-inflammatory compounds. Ten spongian diterpenes were isolated from the New Zealand, sponge Chelonaplysilla violacea, six of which are novel. Cadlinolides C (138) and D (139) are similar to several previously reported compounds while pourewic acid A (140), 15-methoxypourewic acid B (141), methylpourewate B (142) and pourewanone (143) have unique structural features and are of biogenetic significance. Pourewanone (143) is the first example of a formate isolated from the marine environment. Several of the novel diterpenes exhibit moderate anti-inflammatory activity. A potent dinoflagellate toxin was partially purified from cultures of the producing organism, Karenia brevisulcata. K. brevisulcata is a new dinoflagellate species implicated in a large toxic algal bloom in Wellington Harbour, New Zealand, which formed during the summer of 1997/1998. Although the toxin could not be identified, some of the functionality present, and several possible substructures, is proposed. The biological activity of the toxin is also described.</p>

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