Recent Developments on Ultrasound-Assisted Synthesis of Bioactive N-Heterocycles at Ambient Temperature

2017 ◽  
Vol 70 (8) ◽  
pp. 872 ◽  
Author(s):  
Bubun Banerjee

N-Heterocycles represent privileged structural subunits well distributed in naturally occurring compounds with immense biological activities. The last decade has seen a tremendous practice to carry out reactions at ambient temperature avoiding harsh reaction conditions. By applying ultrasonic radiation in organic synthesis we can make synthetic protocols more sustainable and can carry out reactions at room temperature avoiding the traditional thermal harsh reaction conditions. Therefore the synthesis of biologically relevant N-heterocycles at room temperature under the influence of ultrasonic irradiation is one of the advancing areas in the 21st century among organic chemists. The present review summarises the latest developments on ultrasound-assisted synthesis of biologically relevant N-heterocycles at ambient temperature.

2020 ◽  
Vol 24 (22) ◽  
pp. 2601-2611
Author(s):  
Komal Chandrakar ◽  
Jeevan Lal Patel ◽  
S. P. Mahapatra ◽  
Santhosh Penta

Coumarin-linked heterocycles represent privileged structural subunits and are welldistributed in naturally occurring compounds with immense biological activities. Multicomponent reactions (MCRs) are becoming a valuable tool for synthesizing structurally diverse molecular entities. On the other hand, the last year has seen a tremendous outburst in modifying chemical processes to make them sustainable for the betterment of our environment. The application of aqueous medium in organic synthesis is fulfilling some of the goals of ‘green and sustainable chemistry’ as it has some advantages over the traditional synthetic methods in terms of reaction rates, yields, purity of the products, product selectivity, etc. Hence, significant progress has been made in recent years. In the present review, we provide an overview of the recent developments of multicomponent synthesis of biologically relevant coumarin linked and fused heterocyclic compounds carried out from 2015 till today in an aqueous medium.


2017 ◽  
Vol 82 (7-8) ◽  
pp. 755-790 ◽  
Author(s):  
Bubun Banerjee

In the recent past, a number of methods were reported on the application of ultrasound in organic reactions for the synthesis of diverse organic scaffolds. On the other hand, as far as green chemistry is concerned, water is the safest of all solvents. Thus, a ?strong collaboration? between ultrasonic irradiation and aqueous medium holds the key to the development of an environmentally sustainable protocol. The present review summarizes the latest developments in ultrasound-assisted and water-mediated organic synthesis reported to date.


2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.


2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.


Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1966-1970 ◽  
Author(s):  
Giulia Oss ◽  
Thanh Vinh Nguyen

The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.


2020 ◽  
Vol 24 (6) ◽  
pp. 583-621
Author(s):  
Arvind Singh ◽  
Gurpreet Kaur ◽  
Bubun Banerjee

Bis(indolyl)methane skeleton is the main building block of many naturally occurring bioactive compounds. Bis(indolyl)methanes are found to possess a wide range of pharmaceuitical efficacies. These important scaffolds are being used as anti-cancer, antioxidant, anti-bacterial, anti-inflammatory, and anti-proliferative agents. In this review, we summarized the latest developments on the synthesis of various bis/tris(indolyl)methane derivatives from the reactions of two equivalents of indoles and one equivalent of aldehydes or indole-3-carbaldehydes under various reaction conditions. More than hundred different catalysts were employed for these transformations which include various metal catalysts, ionic liquids, organocatalysts, surfactants, homogeneous, heterogeneous catalysts etc.


2020 ◽  
Vol 23 (28) ◽  
pp. 3137-3153 ◽  
Author(s):  
Sankuviruthiyil M. Ujwaldev ◽  
K. R. Rohit ◽  
Sankaran Radhika ◽  
Gopinathan Anilkumar

: Transition metal catalyzed cross-coupling reactions have always been very important in synthetic organic chemistry due to their versatility in forming all sorts of carbon-carbon and carbon-hetero atom bonds. Incorporation of ultrasound assistance to these protocols resulted in milder reaction conditions, faster reaction rates, etc. This review focuses on the contributions made by ultrasound-assisted protocols towards transition metal catalyzed crosscoupling reactions.


2009 ◽  
Vol 87 (9) ◽  
pp. 1209-1212 ◽  
Author(s):  
Hongshe Wang ◽  
June Zeng

Chalcones are useful intermediates in organic synthesis and exhibit a large number of different biological activities. Chalcones have been synthesized in high yields by Claisen–Schmidt condensation of substituted acetophenones with various aromatic aldehydes in the presence of 10 mol% of iodine at room temperature by grinding under solvent-free conditions.


Foods ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1207
Author(s):  
Ernesto R. Soto ◽  
Florentina Rus ◽  
Hanchen Li ◽  
Carli Garceau ◽  
Jeffrey Chicca ◽  
...  

Terpenes are naturally occurring compounds produced by plants that are of great commercial interest in the food, agricultural, cosmetic, and pharmaceutical industries due to their broad spectra of antibacterial, antifungal, anthelmintic, membrane permeation enhancement, and antioxidant biological activities. Applications of terpenes are often limited by their volatility and the need for surfactants or alcohols to produce stable, soluble (non-precipitated) products. Yeast particles (YPs) are hollow, porous microspheres that have been used for the encapsulation of terpenes (YP terpenes) by passive diffusion of terpenes through the porous YP cell walls. We here report the development of a second generation YP encapsulated terpene technology that incorporates the stimuli-responsive control of terpene release using biodegradable pro-terpene compounds (YP pro-terpenes). YP terpenes and YP pro-terpenes were both produced, in which high levels of carvacrol, eugenol, thymol and geraniol were encapsulated. The YP pro-terpenes show higher encapsulation stability than YP terpenes due to pro-terpenes being non-volatile solids at room temperature and stable in suspensions at neutral pH. YP pro-terpenes and YP terpenes were evaluated for biological activity in antibacterial, antifungal and anthelmintic assays. The YP pro-terpenes retained the full biological activity of the parent terpene compound.


Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1071
Author(s):  
Savvas N. Georgiades ◽  
Persefoni G. Nicolaou ◽  
Nikos Panagiotou

The availability and application of direct, functional group-compatible C–H activation methods for late-stage modification of small-molecule bioactives and other valuable materials remains an ongoing challenge in organic synthesis. In the current study, we demonstrate that a LED-activated, photoredox-mediated, Pd(OAc)2-catalyzed C–H arylation, employing a phenyldiazonium aryl source and either tris(2,2′-bipyridine)ruthenium(II) or (2,2′-bipyridine)bis[3,5-di-fluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kN][phenyl-kC]iridium(III) as photoredox initiator, may successfully produce unprecedented mono- and bis-phenyl derivatives of functionality-rich 2,6-diphenylpyrimidine substrates at room temperature. The series of 19 substrates employed herein, which share the biologically-relevant 4-methyl-2,6-diphenylpyrimidine-5-carboxylate scaffold, were generated via a synthetic route involving (3-component) Biginelli condensation, oxidative dehydrogenation of the obtained 3,4-dihydropyrimidin-2(1H)-one to 2-hydroxypyrimidine, O-sulfonylation, and Suzuki-Miyaura C–C cross-coupling. Submission of these substrates to pyrimidine-N-atom-directed C–H arylation conditions led to regioselective phenylation at the ortho site(s) of the pyrimidine-C2-connected phenyl ring, revealing substituent-dependent electronic and steric effects. A focused library of 18 mono- and 10 bis-phenyl derivatives was generated. Its members exhibit interesting 3D and peripheral substitution features that render them promising for evaluation in drug discovery efforts.


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