DOI QR코드

DOI QR Code

A Practical and Convenient Procedure for the N-Formylation of Amines Using Formic Acid

  • 발행 : 2002.01.20

초록

키워드

참고문헌

  1. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience: New York, 1999.
  2. Sheehan, J. C.; Yang, D. D. H. J. Am. Chem. Soc. 1958, 80, 1154. https://doi.org/10.1021/ja01538a036
  3. Waki, J.; Meienhofer, J. J. Org. Chem. 1977, 42, 2019. https://doi.org/10.1021/jo00431a046
  4. Ugi, I. Angew. Chem. Int. Ed. Engl. 1982, 21, 810. https://doi.org/10.1002/anie.198208101
  5. Schollkopf, U. Angew. Chem. Int. Ed. Engl. 1977, 16, 339 https://doi.org/10.1002/anie.197703393
  6. Effenberger, F.; Eichhorn, J. Tetrahedron: Asymmetry 1997, 8, 469. https://doi.org/10.1016/S0957-4166(96)00528-9
  7. Humber, L. G. J. Med. Chem. 1971, 14, 982. https://doi.org/10.1021/jm00292a024
  8. Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. https://doi.org/10.1016/S0040-4020(98)01097-7
  9. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620. https://doi.org/10.1021/jo00101a021
  10. Kobayashi, S.; Yasuda, M.; Hachiya, I. Chemistry Lett. 1996, 407.
  11. Strazzolini, P.; Giumanini, A. G.; Cauci, S. Tetrahedron 1990, 46, 1081 https://doi.org/10.1016/S0040-4020(01)86676-X
  12. Blicke, F. F.; Lu, C.-J. J. Am. Chem. Soc. 1952, 74, 3933 https://doi.org/10.1021/ja01135a503
  13. Waki, J.; Meienhofer, J. J. Org. Chem. 1977, 42, 2019 https://doi.org/10.1021/jo00431a046
  14. Chen, F. M. F.; Benoiton, N. L. Synthesis 1979, 709
  15. Yale, H. L. J. Org. Chem. 1971, 36, 3238 https://doi.org/10.1021/jo00820a603
  16. Kisfaludy, L.; Laszlo, O. Synthesis 1987, 510
  17. Neveux, M.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc. Perkin Trans. I 1991, 1197
  18. Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996, 37
  19. Reddy, P. G.; Kumar, G. D. K.; Baskaran, S. Tetrahedron Lett. 2000, 41, 9149 https://doi.org/10.1016/S0040-4039(00)01636-1
  20. Fieser, L. F.; Jones, J. E. Org. Synth., Coll. Vol. III 1955, 590

피인용 문헌

  1. -benzoquinonediimine vol.20, pp.8, 2007, https://doi.org/10.1021/tx700040s
  2. Nano-MgO: An Efficient Catalyst for the Synthesis of Formamides from Amines and Formic Acid Under MWI vol.138, pp.1-2, 2010, https://doi.org/10.1007/s10562-010-0372-6
  3. ChemInform Abstract: A Practical and Convenient Procedure for the N-Formylation of Amines Using Formic Acid. vol.33, pp.27, 2010, https://doi.org/10.1002/chin.200227080
  4. -Formylation of Secondary Amines via Reimer–Tiemann Reaction vol.41, pp.4, 2011, https://doi.org/10.1080/00397910903576644
  5. N,N-diformyltrifluoromethanesulfonamide vol.47, pp.12, 2011, https://doi.org/10.1134/S1070428011120281
  6. Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: A novel, practical and convenient ‘NOSE’ approach vol.14, pp.3, 2012, https://doi.org/10.1039/c2gc16020j
  7. Oxidative carbonylation of amines to formamides using NaIO4 vol.48, pp.92, 2012, https://doi.org/10.1039/c2cc36809a
  8. Enzyme-Catalyzed Synthesis of Aliphatic–Aromatic Oligoamides vol.14, pp.5, 2013, https://doi.org/10.1021/bm400243a
  9. -Formylation of Anilines with Silica Sulfuric Acid under Solvent-Free Conditions vol.2013, pp.2090-9071, 2013, https://doi.org/10.1155/2013/972960
  10. A Simple Method for Preparation of ZnO Nanoparticles as a Highly Efficient Nanocatalyst for N-Formylation of Primary and Secondary Amines under Solvent-Free Condition vol.43, pp.5, 2013, https://doi.org/10.1080/15533174.2012.741180
  11. System vol.54, pp.2, 2013, https://doi.org/10.1002/jccs.200700067
  12. Direct Catalytic N-Alkylation of Amines with Carboxylic Acids vol.136, pp.40, 2014, https://doi.org/10.1021/ja5093612
  13. Formylation of Amines vol.19, pp.6, 2014, https://doi.org/10.3390/molecules19067689
  14. -formyl tryptophan hydrobromide vol.20, pp.4, 2014, https://doi.org/10.1002/psc.2613
  15. Selective catalytic transfer hydrogenation of nitriles to primary amines using Pd/C vol.4, pp.3, 2014, https://doi.org/10.1039/c3cy00854a
  16. Catalytic methylation of aromatic amines with formic acid as the unique carbon and hydrogen source vol.50, pp.90, 2014, https://doi.org/10.1039/C4CC05908E
  17. Catalytic N-Alkylation of Amines Using Carboxylic Acids and Molecular Hydrogen vol.137, pp.42, 2015, https://doi.org/10.1021/jacs.5b07994
  18. -Formylating Reagent for Amines, Amino Acids, and Peptides vol.19, pp.18, 2017, https://doi.org/10.1021/acs.orglett.7b02382
  19. -formylation of various amines and its biological activity studies vol.31, pp.12, 2017, https://doi.org/10.1002/aoc.3874
  20. Co3O4 nanoparticles prepared by oxidative precipitation method: an efficient and reusable heterogeneous catalyst for N-formylation of amines vol.43, pp.1, 2017, https://doi.org/10.1007/s11164-016-2631-7
  21. Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO vol.25, pp.6, 2018, https://doi.org/10.1002/chem.201805307
  22. Microwave enhanced reduction of nitro and azido arenes to N-arylformamides employing Zn–HCOONH4: synthesis of 4(3H)-quinazolinones and pyrrolo[2,1-c][1,4]benzodiazepines vol.45, pp.34, 2002, https://doi.org/10.1016/j.tetlet.2004.06.112
  23. Thermal and microwave-assisted N-formylation using solid-supported reagents vol.46, pp.6, 2002, https://doi.org/10.1016/j.tetlet.2004.12.044
  24. Microwave promoted energy-efficient N-formylation with aqueous formic acid vol.47, pp.27, 2002, https://doi.org/10.1016/j.tetlet.2006.04.148
  25. ZnO as a New Catalyst for N-Formylation of Amines under Solvent-Free Conditions vol.71, pp.17, 2002, https://doi.org/10.1021/jo060847z
  26. A practical synthesis of the 13 C/ 15 N-labelled tripeptide N -formyl-Met-Leu-Phe, useful as a reference in solid-state NMR spectroscopy vol.4, pp.None, 2008, https://doi.org/10.3762/bjoc.4.35
  27. New Route to N-Formylation of Primary Amines with Amino Acids as a Source of CO Using Polyaniline Catalyst vol.30, pp.10, 2009, https://doi.org/10.5012/bkcs.2009.30.10.2377
  28. Sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe2O3 nanocrystallites as a magnetically Brønsted acid for N-formylation of amines vol.377, pp.1, 2002, https://doi.org/10.1016/j.apcata.2010.01.020
  29. A very simple and highly efficient procedure for N-formylation of primary and secondary amines at room temperature under solvent-free conditions vol.51, pp.17, 2002, https://doi.org/10.1016/j.tetlet.2010.02.119
  30. Convenient N-Formylation of Amines in Dimethylformamide with Methyl Benzoate under Microwave Irradiation vol.31, pp.5, 2002, https://doi.org/10.5012/bkcs.2010.31.5.1424
  31. Solvent-free Zinc-catalyzed Amine N-Formylation vol.31, pp.10, 2002, https://doi.org/10.5012/bkcs.2010.31.10.2989
  32. An Efficient Method for N-Formylation of Amines Using Natural HEU Zeolite at Room Temperature Under Solvent-Free Conditions vol.33, pp.7, 2012, https://doi.org/10.5012/bkcs.2012.33.7.2251
  33. Efficient Synthesis of 4h-Benzo[d][1,3]oxazin-4-ones from Anthranilic Acids and Aryl Isoselenocyanates vol.37, pp.6, 2002, https://doi.org/10.3184/174751913x13686242406479
  34. Synthesis and structural study of precursors of novel methylsilanediols by IR and Raman spectroscopies, single-crystal X-ray diffraction and DFT calculations vol.118, pp.None, 2002, https://doi.org/10.1016/j.saa.2013.09.032
  35. General Catalytic Methylation of Amines with Formic Acid under Mild Reaction Conditions vol.20, pp.26, 2002, https://doi.org/10.1002/chem.201402124
  36. A Practical and General Base‐Catalyzed Carbonylation of Amines for the Synthesis of N‐Formamides vol.21, pp.42, 2015, https://doi.org/10.1002/chem.201502107
  37. Preparation, characterization and application of nanosized CuO/HZSM-5 as an efficient and heterogeneous catalyst for the N-formylation of amines at room temperature vol.471, pp.None, 2002, https://doi.org/10.1016/j.jcis.2016.02.062
  38. Recent developments on ultrasound assisted catalyst-free organic synthesis vol.35, pp.1, 2017, https://doi.org/10.1016/j.ultsonch.2016.09.023
  39. Understanding and Kinetic Modeling of Complex Degradation Pathways in the Solid Dosage Form: The Case of Saxagliptin vol.11, pp.9, 2002, https://doi.org/10.3390/pharmaceutics11090452
  40. Recent advances in N-formylation of amines and nitroarenes using efficient (nano)catalysts in eco-friendly media vol.21, pp.19, 2019, https://doi.org/10.1039/c9gc01822k
  41. Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones vol.18, pp.29, 2002, https://doi.org/10.1039/d0ob01080d
  42. Silver-Catalyzed, N-Formylation of Amines Using Glycol Ethers vol.85, pp.20, 2020, https://doi.org/10.1021/acs.joc.0c01552
  43. Efficient N-formylation of primary aromatic amines using novel solid acid magnetic nanocatalyst vol.10, pp.67, 2002, https://doi.org/10.1039/d0ra07476d
  44. Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd@MCP) for chemoselective N-formylation and N-acylation of amines vol.1225, pp.None, 2002, https://doi.org/10.1016/j.molstruc.2020.129076
  45. Zirconium-containing metal organic frameworks as solid acid catalysts for the N-formylation of aniline with formic acid vol.133, pp.1, 2021, https://doi.org/10.1007/s11144-021-01982-1