Photochemical Acylation of 1,4-Naphthoquinone with Aldehydes Under Continuous-Flow Conditions

References (60)

1. 1 Jha, 2024, Direct Functionalization of para-Quinones: A Historical Review and New Perspectives [DOI]
2. 2 Mone, N.S., Bhagwat, S.A., Sharma, D., Chaskar, M., Patil, R.H., Zamboni, P., Nawani, N.N., and Satpute, S.K. (2021). Naphthoquinones and Their Derivatives: Emerging Trends in Combating Microbial Pathogens. Coatings, 11. [DOI]
3. 3 Ahmadi, 2020, Naphthoquinone Derivatives Isolated from Plants: Recent Advances in Biological Activity [DOI]
4. 4 Leyva, 2011, Naphthoquinones: More than Natural Pigments
5. 5 Jang, 2024, Visible Light Induced Reactions of Quinones [DOI]
6. 6 Ando, 2018, Photoredox Reactions of Quinones [DOI]
7. 7 Ferreira, 2015, Fotoquímica de Naftoquinonas
8. 8 Sapre, 2000, Photo and Radiation Chemistry of Quinones
9. 9 Patai, 1988, Recent Advances in the Photochemistry of Quinones
10. 10 Mitchell, 2013, Solar Photochemistry: Optimisation of the Photo Friedel–Crafts Acylation of Naphthoquinones [DOI]
11. 11 Benites, 2011, The Solar-chemical Photo-Friedel–Crafts Heteroacylation of 1,4-Quinones [DOI]
12. 12 Horspool, W.M., and Lenci, F. (2004). The “Photochemical Friedel-Crafts Acylation” of Quinones: From the Beginnings of Organic Photochemistry to Modern Solar Chemical Applications. CRC Handbook of Organic Photochemistry and Photobiology, CRC Press. [2nd ed.]. Chapter 88.
13. 13 Benites, J., Valderrama, J.A., Contreras, Á., Enríquez, C., Pino-Rios, R., Yáñez, O., and Calderon, P.B. (2023). Discovery of New 2-Phenylamino-3-acyl-1,4-naphthoquinones as Inhibitors of Cancer Cells Proliferation: Searching for Intra-Cellular Targets Playing a Role in Cancer Cells Survival. Molecules, 28. [DOI]
14. 14 Araya, G., Benites, J., Reyes, J.S., Marcoleta, A.E., Valderrama, J.A., Lagos, R., and Monasterio, O. (2019). Inhibition of Escherichia coli and Bacillus subtilis FtsZ Polymerization and Bacillus subtilis Growth by Dihydroxynaphtyl Aryl Ketones. Front. Microbiol., 10. [DOI]
15. 15 Xia, 2014, Anti-tyrosinase, Antioxidant, and Antibacterial Activities of Novel 5-Hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans [DOI]
16. 16 Pedroza, 2014, The cytotoxic Effect of 2-Acylated-1,4-naphthohydroquinones on Leukemia/Lymphoma Cells [DOI]
17. 17 Maruyama, 1974, Photo-induced Condensation Reaction of p-Quinones with Aldehydes [DOI]
18. 18 Albini, 2021, Norrish’ Type I and II Reactions and their Role in the Building of Photochemical Science [DOI]
19. 19 Schiel, 2002, The “Photo-Friedel-Crafts Acylation” of 1,4-Naphthoquinones [DOI]
20. 20 Dekker, 1968, Photodimerization. I. The syn and anti-Photodimers of 1,4-Naphthoquinone [DOI]
21. 21 Newman, S.G. (2023). Introduction to Photochemistry for the Synthetic Chemist. Enabling Tools and Techniques for Organic Synthesis: A Practical Guide to Experimentation, Automation, and Computation, John Wiley & Sons Ltd.. Chapter 2.
22. 22 Evans, R.C., Douglas, P., and Burrows, H.D. (2013). The Photochemical Laboratory. Applied Photochemistry, Springer. Chapter 14. [DOI]
23. 23 Bochet, 2019, On the Sustainability of Photochemical Reactions [DOI]
24. 24 Ravelli, 2013, Visible Light Photocatalysis. A Green Choice? [DOI]
25. 25 Koeberg, 2024, Paradigm Shift in Medicinal Products Synthesis: Continuous Flow Technology [DOI]
26. 26 Alfano, 2024, Continuous Flow Synthesis enabling Reaction Discovery [DOI]
27. 27 Alfano, 2023, Continuous-Flow Technology for Chemical Rearrangements: A Powerful Tool to Generate Pharmaceutically Relevant Compounds [DOI]
28. 28 Srivastava, 2024, Continuous-Flow Photochemistry: The Synthesis of Marketed Pharmaceutical Compounds [DOI]
29. 29 Fukuyama, 2022, Improved Efficiency of Photo-induced Synthetic Reactions Enabled by Advanced Photo Flow Technologies [DOI]
30. 30 Politano, 2018, Light on the Horizon: Current Research and Future Perspectives in Flow Photochemistry [DOI]
31. 31 Rehm, 2020, Flow Photochemistry as a Tool in Organic Synthesis [DOI]
32. 32 Hoffmann, 2014, From ‘Lab & Light on a Chip’ to Parallel Microflow Photochemistry [DOI]
33. 33 Zhang, 2023, Flow photochemistry—From Microreactors to Large-scale Processing [DOI]
34. 34 Yaseen, M.A., Guo, Z., Junk, P.J., and Oelgemöller, M. (2024). [2+2]-Photocycloadditions of 1,4-Naphthoquinone Under Batch and Continuous-Flow Conditions. Molecules, 29. [DOI]
35. 35 Khan, 2024, Optimization of Blue LED Photo-Flow Synthesis in Continuous Flow Reactors Using Design of Experiments (DoE): Efficient Synthesis of Diverse Diaryl Ketones [DOI]
36. 36 Yaseen, 2020, Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor [DOI]
37. 37 Marteaua, 2013, Oxidative Degradation of Fragrant Aldehydes. Autoxidation by Molecular Oxygen [DOI]
38. 38 Mumtaz, S., Robertson, M.J., and Oelgemöller, M. (2019). Continuous Flow Photochemical and Thermal Multi-step Synthesis of Bioactive 3-Arylmethylene-2,3-dihydro-1H-isoindolin-1-ones. Molecules, 24. [DOI]
39. 39 Helferich, 1926, Zur Synthese von Disacchariden IV. Zwei Tetra-acetyl-β-d-glucosen [DOI]
40. 40 Kraus, 1992, Quinone Photochemistry. A General Synthesis of Acylhydroquinones [DOI]
41. 41 Jha, 2022, Light-Driven Carbon−Carbon Coupling of α-sp3−CH of Aliphatic Alcohols with sp2−CH Bond of 1,4-Naphthoquinones [DOI]
42. 42 Hase, 1955, Antibacterial Properties of Naphthoquinones. I. Syntheses and Antibacterial Properties of Acylnaphthoquinones [DOI]
43. 43 Maruyama, 1980, Photo-oxygenation of Alkenoyl-1,4-quinones by Atmospheric Oxygen. Formation of Stable Cyclic Peroxides [DOI]
44. 44 Batley, 1984, Use of Teflon Components in Photochemical Reactors [DOI]
45. 45 Friedrichs, 2008, An improved Procedure for the Photoacylation of 1,4-Naphthoquinone with Aliphatic Aldehydes
46. 46 Mercier, 2024, Synthesis of Acylated Naphthohydroquinones through Photo-Friedel-Crafts Acylation and Evaluation of their Antibiotic Potential [DOI]
47. 47 Chen, 2015, When Solids Stop Flow Chemistry in Commercial Tubing [DOI]
48. 48 Wernerova, 2010, On the Practical Limits of Determining Isolated Product Yields and Ratios of Stereoisomers: Reflections, Analysis, and Redemption
49. 49 Das, 2005, Hydrogen Abstraction from Solvents by the Triplet State of p-Benzoquinone: A Time-resolved Electron Paramagnetic Resonance and Laser Flash Photolysis Study [DOI]
50. 50 Supplement, B., and Patai, S. (1979). The Photochemistry of Organic Acids, Esters, Anhydrides, Lactones and Imides. The Chemistry of Acid Derivatives, John Wiley & Sons Ltd.. Part 1, Chapter 11.
51. 51 Capello, 2007, What is a Green Solvent? A Comprehensive Framework for the Environmental Assessment of Solvents [DOI]
52. 52 Montalti, M., Credi, A., Prodi, L., and Gandolfi, M.T. (2006). Handbook of Photochemistry, CRC Press. [3rd ed.]. [DOI]
53. 53 Bunce, 1977, On the Excited States of p-Quinones and an Interpretation of the Photocycloaddition of p-Quinones to Alkenes [DOI]
54. 54 Kraus, 1994, Benzophenone-Mediated Conjugate Additions of Aromatic Aldehydes to Quinones [DOI]
55. 55 McDowell, 1962, Isomerization as a Primary Process in the Photolysis of Crotonaldehyde [DOI]
56. 56 Otake, 2018, Recent Advances in the Integrated Micro-flow Synthesis Containing Photochemical Reactions [DOI]
57. 57 Spruit, 1947, Carbonyl-substituted Naphthoquinones. Part I. Methyl Ketones Unsubstituted in the Side Chain [DOI]
58. 58 Derikvand, 2010, Oxidation of Hydroquinones to Benzoquinones with Hydrogen Peroxide using Catalytic Amount of Silver Oxide under Batch and Continuous-flow Conditions [DOI]
59. 59 Donnelly, 2021, Scalability of Photochemical Reactions in Continuous Flow Mode [DOI]
60. 60 Hunter, 2018, Rapid Photochemical Reaction Studies under Continuous-flow Conditions in the Vapourtec UV-150 Reactor—A Technical Note [DOI]

Cited by 6

Showing 2 of 6 known citations — external sources report more than can currently be individually listed.

Related research

• A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
• Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
• Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
• Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
• Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage