Recent Advances in the Synthesis of Heterocycles by the Aza-Wittig Reaction

Synthesis ◽  
2021 ◽  
Author(s):  
Mohammad Mahdavi ◽  
Keyvan Pedrood ◽  
Mohammad Nazari Montazer ◽  
Bagher Larijani
Keyword(s):  
Heterocyclic Compounds ◽  
Wittig Reaction ◽  
Recent Advances ◽  
Wide Range ◽  
Wittig Reactions

AbstractThe formation of the C=N bond in recent studies on heterocyclic compounds via the aza-Wittig reaction is reviewed. Furthermore, two different strategies for the formation of heterocyclic compounds, including intermolecular and intramolecular aza-Wittig reactions are described. The primary aim of this review is to provide up-to-date information on the application of the aza-Wittig reaction in the synthesis of a wide range of N-containing heterocyclic compounds in the chemical literature since 2010.1 Introduction2 Mechanism of the Staudinger and Aza-Wittig Reactions3 Intramolecular Aza-Wittig Reaction4 Intermolecular Aza-Wittig Reaction5 Conclusion

scholarly journals Recent advances in catalytic Wittig-type reactions based on P(III)/P(V) redox cycling

2019 ◽  
Vol 91 (1) ◽  
pp. 95-102 ◽  
Author(s):  
Lars Longwitz ◽  
Thomas Werner
Keyword(s):  
Driving Force ◽  
Wittig Reaction ◽  
Redox Cycling ◽  
Organic Transformations ◽  
Microwave Assisted ◽  
Recent Advances ◽  
Thermodynamic Driving Force ◽  
Wittig Reactions ◽  
By Products

Abstract Numerous organic transformations are based on the use of stoichiometric amounts of phosphorus reagents. The formation of phosphane oxides from phosphanes is usually the thermodynamic driving force for these reactions. The stoichiometric amounts of phosphane oxide which are formed as by-products often significantly hamper the product purification. Organophosphorus catalysis based on P(III)/P(V) redox cycling aims to address these problems. Herein we present our recent advances in developing catalytic Wittig-type reactions. More specifically, we reported our results on catalytic Wittig reactions based on readily available Bu3P=O as pre-catalyst as well as the first microwave-assisted version of this reaction and the first enantioselective catalytic Wittig reaction utilizing chiral phosphane catalysts. Further developments led to the implementation of catalytic base-free Wittig reactions yielding highly functionalized alkylidene and arylidene succinates.

Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3818-3836
Author(s):  
Jin-Heng Li ◽  
De-Lie An ◽  
Jing-Hao Qin
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reactions ◽  
Structural Motifs ◽  
Recent Advances ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spirohetero­cyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

A REVIEW ON RECENT ADVANCES IN CHEMISTRY, SYNTHESIS AND BIOLOGICAL APPLICATIONS OF ISATIN DERIVATIVES

2018 ◽  
pp. 16-22
Author(s):  
Shukla PK ◽  
Singh MP ◽  
Patel R
Keyword(s):  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Biological Applications ◽  
Plant Origin ◽  
Recent Past ◽  
Pharmacological Activities ◽  
Naturally Occurring ◽  
Recent Advances ◽  
Biological Aspects ◽  
Isatin Derivatives

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.

Heterocycle Compounds with Antimicrobial Activity

2020 ◽  
Vol 26 (8) ◽  
pp. 867-904 ◽  
Author(s):  
Maria Fesatidou ◽  
Anthi Petrou ◽  
Geronikaki Athina
Keyword(s):  
Heterocyclic Compounds ◽  
Bacterial Infections ◽  
Scientific Community ◽  
Antimicrobial Agents ◽  
Fungal Infections ◽  
Biological Activities ◽  
Literature Survey ◽  
New Findings ◽  
Wide Range ◽  
Number Of Microorganisms

Background: Bacterial infections are a growing problem worldwide causing morbidity and mortality mainly in developing countries. Moreover, the increased number of microorganisms, developing multiple resistances to known drugs, due to abuse of antibiotics, is another serious problem. This problem becomes more serious for immunocompromised patients and those who are often disposed to opportunistic fungal infections. Objective: The objective of this manuscript is to give an overview of new findings in the field of antimicrobial agents among five-membered heterocyclic compounds. These heterocyclic compounds especially five-membered attracted the interest of the scientific community not only for their occurrence in nature but also due to their wide range of biological activities. Method: To reach our goal, a literature survey that covers the last decade was performed. Results: As a result, recent data on the biological activity of thiazole, thiazolidinone, benzothiazole and thiadiazole derivatives are mentioned. Conclusion: It should be mentioned that despite the progress in the development of new antimicrobial agents, there is still room for new findings. Thus, research still continues.

A Brief Review on the Development of Novel Potentially Active Azetidin-2-ones Against Cancer

2020 ◽  
Vol 24 (5) ◽  
pp. 473-486 ◽  
Author(s):  
Ligia S. da Silveira Pinto ◽  
Thatyana R. Alves Vasconcelos ◽  
Claudia Regina B. Gomes ◽  
Marcus Vinícius N. de Souza
Keyword(s):  
Side Effects ◽  
Anticancer Agents ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Present Review ◽  
Pharmacological Properties ◽  
Important Group ◽  
Wide Range ◽  
Anti Inflammatory

Azetidin-2-ones (&#946;-lactams) and its derivatives are an important group of heterocyclic compounds that exhibit a wide range of pharmacological properties such as antibacterial, anticancer, anti-diabetic, anti-inflammatory and anticonvulsant. Efforts have been made over the years to develop novel congeners with superior biological activities and minimal potential for undesirable side effects. The present review aimed to highlight some recent discoveries (2013-2019) on the development of novel azetidin-2-one-based compounds as potential anticancer agents.

The chemistry of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5- ones as a privileged scaffold in synthesis of heterocycles

2020 ◽  
Vol 17 ◽  
Author(s):  
Mohsen A.-M. Gomaa ◽  
Huda A. Ali
Keyword(s):  
Building Block ◽  
Heterocyclic Compounds ◽  
Recent Progress ◽  
Reaction Conditions ◽  
Azacrown Ethers ◽  
Wide Range ◽  
Privileged Scaffold ◽  
Number Of Publications ◽  
Near Future

Background : The reactivity of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5-one DCNP 1 and its derivatives makes it valuable as a building block for the synthesis of heterocyclic compounds like pyrazolo-imidazoles, - thiazoles, spiropyridines, spiropyrroles, spiropyrans and others. As a number of publications have reported on the reactivity of DCNP and its derivatives, we compiled some features of this interesting molecule. Objective: This article aims to review the preparation of DCNP, its reactivity and application in heterocyclic and dyes synthesis. Conclusion: In this review we have provided an overview of recent progress in the chemistry of DCNP and its significance in synthesis of various classes of heterocyclic compounds and dyes. The unique reactivity of DCNP offers unprecedentedly mild reaction conditions for the generation of versatile cynomethylene dyes from a wide range of precursors including amines, α-aminocarboxylic acids, their esters, phenols, malononitriles and azacrown ethers. We anticipate that more innovative transformations involving DCNP will continue to emerge in the near future.

Recent Advances in Therapeutic Applications of Bisbenzimidazoles

2020 ◽  
Vol 16 (4) ◽  
pp. 454-486 ◽  
Author(s):  
Smita Verma ◽  
Vishnuvardh Ravichandiran ◽  
Nihar Ranjan ◽  
Swaran J.S. Flora
Keyword(s):  
Heterocyclic Compounds ◽  
Wide Spectrum ◽  
Dna Recognition ◽  
Present Review ◽  
Pharmacological Activities ◽  
Structural Motifs ◽  
Therapeutic Applications ◽  
The Past ◽  
Recent Advances

Nitrogen-containing heterocycles are one of the most common structural motifs in approximately 80% of the marketed drugs. Of these, benzimidazoles analogues are known to elicit a wide spectrum of pharmaceutical activities such as anticancer, antibacterial, antiparasitic, antiviral, antifungal as well as chemosensor effect. Based on the benzimidazole core fused heterocyclic compounds, crescent-shaped bisbenzimidazoles were developed which provided an early breakthrough in the sequence-specific DNA recognition. Over the years, a number of functional variations in the bisbenzimidazole core have led to the emergence of their unique properties and established them as versatile ligands against several classes of pathogens. The present review provides an overview of diverse pharmacological activities of the bisbenzimidazole analogues in the past decade with a brief account of its development through the years.

scholarly journals Recent advances in the chemical transformations of functionalized alkylidenecyclopropanes (FACPs)

2017 ◽  
Vol 53 (44) ◽  
pp. 5935-5945 ◽  
Author(s):  
Liu-Zhu Yu ◽  
Kai Chen ◽  
Zi-Zhong Zhu ◽  
Min Shi
Keyword(s):  
Heterocyclic Compounds ◽  
Chemical Transformations ◽  
Recent Advances

Classification of functionalized alkylidenecyclopropanes (FACPs) and recent chemical transformations for the synthesis of novel and useful polycyclic and heterocyclic compounds.

scholarly journals Recent Advances in Enzymatic and Non-Enzymatic Electrochemical Glucose Sensing

Sensors ◽  
2021 ◽  
Vol 21 (14) ◽  
pp. 4672
Author(s):  
Mohamed H. Hassan ◽  
Cian Vyas ◽  
Bruce Grieve ◽  
Paulo Bartolo
Keyword(s):  
Noble Metals ◽  
Direct Electrochemistry ◽  
Glucose Sensing ◽  
Glucose Sensors ◽  
Diabetic Patients ◽  
Past Century ◽  
Industrial Sectors ◽  
Recent Advances ◽  
Wide Range ◽  
Sensitivity And Selectivity

The detection of glucose is crucial in the management of diabetes and other medical conditions but also crucial in a wide range of industries such as food and beverages. The development of glucose sensors in the past century has allowed diabetic patients to effectively manage their disease and has saved lives. First-generation glucose sensors have considerable limitations in sensitivity and selectivity which has spurred the development of more advanced approaches for both the medical and industrial sectors. The wide range of application areas has resulted in a range of materials and fabrication techniques to produce novel glucose sensors that have higher sensitivity and selectivity, lower cost, and are simpler to use. A major focus has been on the development of enzymatic electrochemical sensors, typically using glucose oxidase. However, non-enzymatic approaches using direct electrochemistry of glucose on noble metals are now a viable approach in glucose biosensor design. This review discusses the mechanisms of electrochemical glucose sensing with a focus on the different generations of enzymatic-based sensors, their recent advances, and provides an overview of the next generation of non-enzymatic sensors. Advancements in manufacturing techniques and materials are key in propelling the field of glucose sensing, however, significant limitations remain which are highlighted in this review and requires addressing to obtain a more stable, sensitive, selective, cost efficient, and real-time glucose sensor.

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