An expedient ultrasonic assisted one-pot four component synthesis of novel ferrocene grafted pyrrolidine heterocycles via [3 + 2]-cycloaddition of azomethine ylides
“…1 ). This is a continuation of our group’s research in cycloaddition reactions 52 , 56 , 57 , 59 – 62 . Figure 1 Representation of One-pot synthesis of highly substituted spiroheterocyles containing oxindole and pyrrolidine moieties using dehydroacetic acid based chalcone derivatives 1 (a–e), isatin 2 and sarcosine 3.…”
Section: Resultsmentioning
confidence: 53%
“…The potential of these heterocyclic entities has encouraged us to synthesize hybrid heterocyclic systems incorporating dehydroacetic acid, oxindole and pyrrolidine in a single molecule. The syntheses of the products were accomplished in one pot without using catalyst or any specific reaction conditions in order to improve the yield of the products unlike some other complex multicomponent component reactions which we have previously carried out 53 – 57 . The yields of the products were also satisfactory without employing such strategy.…”
The current work involves the use of dehydroacetic acid based chalcone derivatives for the synthesis of spirooxindole grafted pyrrolidine moieties. All the synthesized compounds have been characterized using spectroscopic techniques such as NMR (1H-NMR and 13C-NMR), IR, mass and elemental analysis. Molecular mechanics studies were performed to comprehend the regioselectivity in the product formation. Molecular docking of the synthesized compounds was performed with few bacterial proteins of Bacillus subtilis and Pseudomonas aeruginosa responsible for biofilm formation followed by molecular dynamics simulations with the potential lead compound. Further, to corroborate the results obtained via in silico study, anti-biofilm activity etc. of the synthesized compounds (4a–e) was checked for effectiveness against biofilm formation. Taken together, this study opens up to explore these compounds’ multiple roles in diverse fields in the arena of medical sciences.
“…1 ). This is a continuation of our group’s research in cycloaddition reactions 52 , 56 , 57 , 59 – 62 . Figure 1 Representation of One-pot synthesis of highly substituted spiroheterocyles containing oxindole and pyrrolidine moieties using dehydroacetic acid based chalcone derivatives 1 (a–e), isatin 2 and sarcosine 3.…”
Section: Resultsmentioning
confidence: 53%
“…The potential of these heterocyclic entities has encouraged us to synthesize hybrid heterocyclic systems incorporating dehydroacetic acid, oxindole and pyrrolidine in a single molecule. The syntheses of the products were accomplished in one pot without using catalyst or any specific reaction conditions in order to improve the yield of the products unlike some other complex multicomponent component reactions which we have previously carried out 53 – 57 . The yields of the products were also satisfactory without employing such strategy.…”
The current work involves the use of dehydroacetic acid based chalcone derivatives for the synthesis of spirooxindole grafted pyrrolidine moieties. All the synthesized compounds have been characterized using spectroscopic techniques such as NMR (1H-NMR and 13C-NMR), IR, mass and elemental analysis. Molecular mechanics studies were performed to comprehend the regioselectivity in the product formation. Molecular docking of the synthesized compounds was performed with few bacterial proteins of Bacillus subtilis and Pseudomonas aeruginosa responsible for biofilm formation followed by molecular dynamics simulations with the potential lead compound. Further, to corroborate the results obtained via in silico study, anti-biofilm activity etc. of the synthesized compounds (4a–e) was checked for effectiveness against biofilm formation. Taken together, this study opens up to explore these compounds’ multiple roles in diverse fields in the arena of medical sciences.
“…As was introduced in section , decarboxylation is a relatively mild and powerful strategy for the generation of semistabilized 2-azaallyl anions. Similarly, the tandem iminium condensation/thermal decarboxylation reaction manifold (via carboxylic acids 278 , Scheme ) is a popular method for in situ preparation of N -alkyl azomethine ylides. − In 1993, Prato and co-workers demonstrated that C 60 could be converted to the corresponding pyrrolidine by 1,3-dipolar cycloaddition with the N -methyl azomethine ylide generated via thermal decarboxylation of the iminium formed by condensation between sarcosine ( N -methlyglycine) and formaldehyde (Scheme ). This so-called “Prato reaction”, and variations thereof, have since been applied toward the functionalization of fullerenes, − graphene and single-walled carbon nanotubes and nanohorns, − …”
This review covers the use of 2-azaallyl
anions, 2-azaallyl cations,
and 2-azaallyl radicals in organic synthesis up through June 2018.
Particular attention is paid to both foundational studies and recent
advances over the past decade involving semistabilized and nonstabilized
2-azaallyl anions as key intermediates in various carbon–carbon
and carbon–heteroatom bond-forming processes. Both transition-metal-catalyzed
and transition-metal-free transformations are covered. Azomethine
ylides, which have received significant attention elsewhere, are discussed
briefly with the primary focus on critical comparisons with 2-azaallyl
anions in regard to generation and use.
“…The Raghunathan group developed an expedient one-pot, four-component synthesis of ferrocene-grafted spiropyrrolidine heterocycles 336 that was assisted by ultrasonic treatment . A solution of the ferrocene-derived dipolarophile 335 , ninhydrin 332 , 1,2-phenylenediamine 333 , and sarcosine 334 in MeOH was sonicated under refluxing conditions for 1 to 2 h to afford the desired complexes with high yield and high regioselectivity, as confirmed by X-ray diffraction (Scheme ).…”
Organometallic complexes: these two words jump to the mind of the chemist and are directly associated with their utility in catalysis or as a pharmaceutical. Nevertheless, to be able to use them, it is necessary to synthesize them, and it is not always a small matter. Typically, synthesis is via solution chemistry, using a roundbottom flask and a magnetic or mechanical stirrer. This review takes stock of alternative technologies currently available in laboratories that facilitate the synthesis of such complexes. We highlight five such technologies: mechanochemistry, also known as solvent-free chemistry, uses a mortar and pestle or a ball mill; microwave activation can drastically reduce reaction times; ultrasonic activation promotes chemical reactions because of cavitation phenomena; photochemistry, which uses light radiation to initiate reactions; and continuous flow chemistry, which is increasingly used to simplify scaleup. While facilitating the synthesis of organometallic compounds, these enabling technologies also allow access to compounds that cannot be obtained in any other way. This shows how the paradigm is changing and evolving toward new technologies, without necessarily abandoning the round-bottom flask. A bright future is ahead of the organometallic chemist, thanks to these novel technologies.
CONTENTS1. Introduction 7530 2. Technologies 7530 2.1. Grinding and Milling 7530 2.2. Microwave Irradiation 7531 2.3. Ultrasound Activation 7531 2.4. Photochemistry 7532 2.5. Continuous Flow 7532 3. Contribution of Each Technology Compared to Classical Syntheses 7533 4. Lithium and Magnesium 7534 4.1. Mechanochemical Access to Grignard Reagents 7534 4.2. Microwave Irradiation for the Synthesis of Magnesium Complexes 7534 4.3. Ultrasonic Procedures 7535 4.4. Continuous Flow Syntheses 7535 5. Groups 2, 3, 4, and 5 7537 5.1. Mechanochemical Procedures for Complexes of Groups 2, 3, and 4 7537 5.2. Microwave Irradiation for the Synthesis of Vanadium Complexes 7537 5.3. Synthesis of Vanadium Complexes Using Ultrasound 7538 6. Group 6 7538 6.1. Mechanosynthesis of Molybdenum and Chromium Complexes 7538 6.2. Microwave Irradiation for the Synthesis of Group 6 Metal Complexes 7539 6.3. Photochemistry for Synthesis of Group 6 Metal Complexes 7543 6.4. Continuous Flow Chemistry for Synthesis of Chromium Complexes 7545 7. Group 7 7545 7.1. Mechanosynthesis of Rhenium Complexes 7545 7.2. Microwave Irradiation for the Synthesis of Group 7 Metal Complexes 7546 7.3. Photochemical Synthesis of Manganese and Rhenium Complexes 7549 8. Group 8 7550 8.1. Synthesis of Iron and Ruthenium Complexes Using Ball Milling 7550 8.2. Microwave Procedures 7552 8.3. Ultrasonic Irradiation for Iron Complexes 7562 8.4. Syntheses of Iron and Ruthenium Complexes Using Photochemistry 7563 8.5. Continuous Flow Conditions to Prepare Iron and Ruthenium Complexes 7566 9. Group 9 7566 9.1. Synthesis of Cobalt and Rhodium Complexes by Mechanochemistry 7566 9.2. Procedures Using Microwave Irradiation 7569 9.3. Photochemical Synthesis of Iridium Complexes 7...
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