scholarly journals Synthesis of heterocyclic compounds using ring-closing enyne metathesis reaction

2020 ◽  
Vol 22 ◽  
pp. 20-29
Author(s):  
Titas Biswas ◽  
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Molecular Complexity ◽  
The Creation ◽  
Key Steps

Ring-closing enyne metathesis reaction has emerged as an elegant tool in organic synthesis for the creation of molecular complexity and used to prepare diverse heterocycles. In this mini review, I discuss that various linearly and angularly architecture heterocyclic compounds may be prepared using RCEM as key steps.

Ionic Liquids for the Synthesis of Five-Membered N,N-, N,N,N- and N,N,N,NHeterocycles

2019 ◽  
Vol 23 (11) ◽  
pp. 1214-1238 ◽  
Author(s):  
Navjeet Kaur ◽  
Pranshu Bhardwaj ◽  
Meenu Devi ◽  
Yamini Verma ◽  
Neha Ahlawat ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Reaction Medium ◽  
Environmental Issues ◽  
Organic Reaction ◽  
Environment Friendly ◽  
The Past ◽  
Area Of Interest ◽  
Major Subject

Due to special properties of ILs (Ionic Liquids) like their wide liquid range, good solvating ability, negligible vapour pressure, non-inflammability, environment friendly medium, high thermal stability, easy recycling and rate promoters etc. they are used in organic synthesis. The investigation for the replacement of organic solvents in organic synthesis is a growing area of interest due to increasing environmental issues. Therefore, ionic liquids have attracted the attention of chemists and act as a catalyst and reaction medium in organic reaction with high activity. There is no doubt that ionic liquids have become a major subject of study for modern chemistry. In comparison to traditional processes the use of ionic liquids resulted in improved, complimentary or alternative selectivities in organic synthesis. The present manuscript reported the synthesis of multiple nitrogen containing five-membered heterocyclic compounds using ionic liquids. This review covered interesting discoveries in the past few years.

Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

2019 ◽  
Vol 16 (6) ◽  
pp. 527-543 ◽  
Author(s):  
Pedro M.E. Mancini ◽  
Carla M. Ormachea ◽  
María N. Kneeteman
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Ionic Conduction ◽  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
The Other ◽  
Conventional Heating ◽  
Protic Ionic Liquids ◽  
Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

scholarly journals Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides

2010 ◽  
Vol 6 ◽  
Author(s):  
Satoru Arimitsu ◽  
Gerald B Hammond
Keyword(s):  
Building Blocks ◽  
Alder Reaction ◽  
Diels Alder ◽  
Tandem Reaction ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Diels Alder Reaction

gem-Difluoro-1,7-enyne amides are suitable building blocks for the synthesis of difluorodihydropyridinones via a ring-closing metathesis reaction, and of 4,4-difluoro-3-oxoisoquinolines through a ring-closing metathesis–enyne metathesis tandem reaction. These products, in turn, undergo a Diels–Alder reaction to yield heterotricyclic systems in moderate to good yields.

scholarly journals A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring-closing metathesis

2009 ◽  
Vol 5 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
Krishnarao Lopinti ◽  
K L N Reddy
Keyword(s):  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Propargylic Alcohol ◽  
Key Steps

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira’s asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the powerful ring-closing metathesis reaction.

scholarly journals Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

2020 ◽  
Vol 16 ◽  
pp. 738-755
Author(s):  
Valerian Dragutan ◽  
Ileana Dragutan ◽  
Albert Demonceau ◽  
Lionel Delaude
Keyword(s):  
Therapeutic Agents ◽  
Ruthenium Catalysts ◽  
Diels Alder ◽  
Bioactive Molecules ◽  
Enyne Metathesis ◽  
Organic Transformations ◽  
Chemically Modified ◽  
Key Steps ◽  
Powerful Strategy

This account surveys the current progress on the application of intra- and intermolecular enyne metathesis as main key steps in the synthesis of challenging structural motifs and stereochemistries found in bioactive compounds. Special emphasis is placed on ruthenium catalysts as promoters of enyne metathesis to build the desired 1,3-dienic units. The advantageous association of this approach with name reactions like Grignard, Wittig, Diels–Alder, Suzuki–Miyaura, Heck cross-coupling, etc. is illustrated. Examples unveil the generality of such tandem reactions in providing not only the intricate structures of known, in vivo effective substances but also for designing chemically modified analogs as valid alternatives for further therapeutic agents.

Development of a Hydrazine-Catalyzed Carbonyl-Olefin Metathesis Reaction

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1954-1965 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Double Bond ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Type I ◽  
Type Ii ◽  
Metathesis Reaction ◽  
Alternative Strategies ◽  
Potential Applications ◽  
Acid Catalyzed ◽  
New Strategies

Carbonyl-olefin metathesis is a potentially powerful yet underexplored reaction in organic synthesis. In recent years, however, this situation has begun to change, most notably with the introduction of several different catalytic technologies. The development of one of those new strategies, based on hydrazine catalysts and a novel [3+2] paradigm for double bond metathesis, is discussed herein. First, the stage is set with a description of some potential applications of carbonyl-olefin metathesis and a discussion of alternative strategies for this intriguing reaction.1 Introduction2 Potential Applications of Carbonyl-Olefin Metathesis3 Carbonyl-Olefin Metathesis Strategies4 Direct (Type I): Non-Catalytic5 Direct (Type I): Acid-Catalyzed6 Indirect (Type II): Metal Alkylidenes7 Indirect (Type III): Hydrazine-Catalyzed8 Conclusion

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