Synthetic Routes to Quinoline Derivatives:  Novel Syntheses of 3-Butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-Butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline

Atkins, Richard J.; Breen, Gary F.; Crawford, L. P.; Grinter, Trevor J.; Harris, Michael A.; Hayes, Jerome F.; Moores, Clive J.; Saunders, R. N.; Share, Andrew C.; Walsgrove, and Timothy C.; Wicks, Christopher

doi:10.1021/op9700035

Cited by 29 publications

(4 citation statements)

References 16 publications

(32 reference statements)

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“…In amino]quinoline was prepared using NBS in CCl 4 under reflux for 1 h (Scheme 215). 754 Regioselective monobromination of aromatic substrates with NBS was achieved by Rajagopal and co-workers using phosphotungstic acid supported on zirconia as a heterogeneous catalyst. 701 Heropoulos and co-workers conducted bromination with NBS assisted by ultrasound and microwave.…”

Section: Aromatic Bromination Using Nbsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Aromatic Bromination Using Nbsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…An important point to remember is that previously reported small scale literature yields may not be repeatable in large scale batch equipment and route redesign may be required. , While these reactions utilized a single reagent stream, slow addition of one reagent to another or true continuous stirred tank reactor conditions could be explored if there was a benefit to operating at end of reaction conditions in this equipment. It is worth noting that the proposed scale up to generate 80 kg per week in a one gallon reactor represents a 151× scale up over the 25 mL reactor demonstrated here.…”

Section: Testing Of Additional Substratesmentioning

confidence: 99%

“…While batch Gould–Jacobs thermal cyclizations and other high-temperature reactions are well-precedented, it was desirable to develop an alternate method that would avoid some of the issues observed in batch, such as long reaction times, difficulty in achieving desired reaction temperatures, and undesirable solvents such as diphenyl ether or Dowtherm. , The temperatures necessary for these cyclizations require specialized batch equipment that can heat to temperatures as high as 310 °C. Recent large-scale requirements for this type of cyclization published in this journal have avoided this transformation entirely by developing a new synthetic route or effecting the same transformation under acidic conditions with Eaton’s reagent . There are examples of these cyclizations under alternative conditions such as microwaves including examination of microwaves on larger scale in flow, but mostly on smaller scale in plug flow reactors (PFR) with solvent and neat …”

Section: Introductionmentioning

confidence: 99%

How to Convert a Walk-in Hood into a Manufacturing Facility: Demonstration of a Continuous, High-Temperature Cyclization to Process Solids in Flow

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et al. 2014

Org. Process Res. Dev.

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An intramolecular thermal cyclization protocol was developed in a flow reactor to take advantage of the high pressures and temperatures that are easily obtained in small scale autoclave reactors that have been modified to handle slurries. This reactor was equipped with a fill/empty pumping system to enable easy and nearly complete transfer of slurries. The reaction conditions were designed to take advantage of the insolubility of the product in order to separate it from residual starting material by filtration after short reaction times. Recycling of the filtrate maximized the yield and throughput while minimizing decomposition. Recycles were accomplished using a strip to dryness protocol that was easily performed in a rotary evaporator. This new equipment set was designed with lab-hood manufacturing in mind, a minimized footprint, and the system was completely automated for charging, emptying, rinsing, and reacting. Additional efforts for quick screening and alternate modes of addition were also investigated.

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“…Quinolines have attracted the attentions of chemists and biologists because they are key building blocks for the synthesis of biologically active natural products bearing quinoline skeletons . In addition, they are widely used in numerous commercial products, such as, pharmaceuticals, fragrances, and dyes . Molecules bearing quinoline skeletons have wide ranging pharmaceutical activities, for example, they have been reported to have, antituberculosis, antimalarial, anti-inflammatory, anticancer, antibiotic, antihypertensive, platelet derived growth factor receptor tyrosine kinase (PDGF-RTK) inhibitory, and antihuman immunodeficiency virus (HIV) activities .…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of Diverse Pyrrolo[3,4-c]quinoline-1,3-diones and Their Antibacterial Activities

et al. 2014

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With the aim of developing a general and practical method for library production, a novel and efficient two-phase microwave-assisted cascade reaction between isatins and β-ketoamides in [Bmim]BF4/toluene was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones. The features of this methodology are, the use of microwave-assisted rapid synthesis, mild reaction conditions, high yields, operational simplicity, facile product separation, and recyclability. Furthermore, the antibacterial activities of the pyrrolo[3,4-c]quinoline-1,3-dione derivatives produced were evaluated against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) and Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus). These derivatives showed antibacterial activities against Gram-positive strains that were at least equivalent to that against Gram-negative strains. Compound 7{3,5} displayed the most potent antibacterial activity against P. aeruginosa (MIC = 0.5 μg/mL) and greater activity than standard ampicillin (MIC = 1 μg/mL). Compound 7{4,7} exhibited the best inhibitory activity against E. coli and E. aerogenes (MIC = 1 and 0.5 μg/mL), compared with the standard ampicillin (both MICs = 1 μg/mL). The synthesized pyrrolo[3,4-c]quinoline-1,3-diones are expected to be widely used as lead compounds for the development of new antibacterial agents.

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Synthetic Routes to Quinoline Derivatives: Novel Syntheses of 3-Butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-Butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline

Cited by 29 publications

References 16 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

How to Convert a Walk-in Hood into a Manufacturing Facility: Demonstration of a Continuous, High-Temperature Cyclization to Process Solids in Flow

Microwave-Assisted Synthesis of Diverse Pyrrolo[3,4-c]quinoline-1,3-diones and Their Antibacterial Activities

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