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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 4
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Articles

DMF·HCl as a versatile and straightforward N- and O-formylating agent

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Pages 585-592 | Received 30 Aug 2020, Published online: 10 Nov 2020

References

  • Heravi, M. M.; Ghavidel, M.; Mohammadkhani, L. Beyond a Solvent: Triple Roles of Dimethylformamide in Organic Chemistry. RSC Adv. 2018, 8, 27832–27862. DOI: 10.1039/C8RA04985H.
  • Nagata, T.; Obora, Y. N,N-Dimethylformamide-Protected Single-Sized Metal Nanoparticles and Their Use as Catalysts for Organic Transformations. ACS Omega. 2020, 5, 98–103. DOI: 10.1021/acsomega.9b03828.
  • Álvarez, R.; Pérez, M.; Faza, O. N.;. de Lera, A. R. Associative Transmetalation in the Stille Cross-Coupling Reaction to Form Dienes: Theoretical Insights into the Open Pathway. Organometallics. 2008, 27, 3378–3389. DOI: 10.1021/om701267r.
  • Lv, J.; Luo, T.; Zou, D.; Dong, H. Using DMF as Both a Catalyst and Cosolvent for the Regioselective Silylation of Polyols and Diols. Eur. J. Org. Chem. 2019, 2019, 6383–6395. DOI: 10.1002/ejoc.201901195.
  • (a) Mata, L.; Avenoza, A.; Busto, J. H.; Peregrina, J. M.; Chemoselectivity Control in the Reactions of 1,2-Cyclic Sulfamidates with Amines. Chem. Eur. J. 2013, 19, 6831–6839. DOI: 10.1002/chem.201204392. (b) Borah, A.; Goswami, L.; Neog, K.; Gogoi, P. DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones. J. Org. Chem. 2015, 80, 4722–4728. DOI: 10.1021/acs.joc.5b00084.
  • Rajput, A. P.; Girase, P. D. IJPCBS 2012, 3, 25–43.
  • Andrade, M. M.; Barros, M. T. Facile Conversion of O-Silyl Protected Sugars into Their Corresponding Formates Using POCl3·DMF Complex. Tetrahedron. 2004, 60, 9235–9243. DOI: 10.1016/j.tet.2004.07.056.
  • Morimura, S.; Horiuchi, H.; Murayama, K. Vilsmeier Reaction of Phenols. I. Synthesis of Aryl Formates. BCSJ. 1977, 50, 2189–2190. DOI: 10.1246/bcsj.50.2189.
  • Srivastava, V.; Negi, A. S.; Kumar, J. M.; Gupta, M. M. A Simple, Convenient and Chemoselective Formylation of Sterols by Vilsmeier Reagent. Steroids. 2006, 71, 632–638. DOI: 10.1016/j.steroids.2006.03.005.
  • (a) De Luca, L.; Giacomelli, G.; Porcheddu, A.; Salaris, M. Synlett. 2004, (14), 2570–2572. (b) Yang, X. J.; Zhang, Y. S. Melamine Trisulfonic Acid-Catalyzed N-Formylation of Amines under Solvent-Free Conditions. Res. Chem. Intermed. 2013, 39, 2843–2848. DOI: 10.1007/s11164-012-0803-7. (c) Pathare, S. P.; Sawant, R. V.; Akamanchi, K. G. Sulfated Tungstate Catalyzed Highly Accelerated N-Formylation. Tetrahedron. Lett. 2012, 53, 3259–3263. DOI: 10.1016/j.tetlet.2012.04.058. (d) Kim, J. G.; Jang, D. O. Indium-Catalyzed N-Formylation of Amines under Solvent-Free Conditions. Synlett. 2010, 2010, 1231–1234. (e) Hosseini-Sarvari, M.; Sharghi, H. ZnO as a New Catalyst for N-Formylation of Amines under Solvent-Free Conditions. J. Org. Chem. 2006, 71, 6652–6654. DOI: 10.1021/jo060847z. (f) Iranpoor, N.; Firouzabadi, H.; Jamalian, A. Silphos [PCl3 − n(SiO2)n]: A Heterogeneous Phosphine Reagent for Formylation and Acetylation of Alcohols and Amines with Ethyl Formate and Acetate. Tetrahedron. Lett. 2005, 46, 7963–7966. DOI: 10.1016/j.tetlet.2005.09.078. (g) Shekhar, A. C.; Kumar, A. R.; Sathaiah, G.; Paul, V. L.; Sridhar, M.; Rao, P. S. Tetrahedron. Lett. 2009, 50, 7099–7101. DOI: 10.1016/j.tetlet.2009.10.006. (h) Brahmachari, G.; Laskar, S.; Tetrahedron Lett 2010, 51, 2322. (i) Preedasuriyachai, P.; Kitahara, H.; Chavasiri, W.; Sakurai, H. N -Formylation of Amines Catalyzed by Nanogold under Aerobic Oxidation Conditions with MeOH or Formalin. Chem. Lett. 2010, 39, 1174–1176. DOI: 10.1246/cl.2010.1174. (j) Hui, L.; Qi, X.; Chengtao, Y.; Ziqiang, L.; Fuwei, L. Chem. Commun. 2016, 52, 6545–1176.
  • Kraus, M. A. The Formylation of Aliphatic Amines by Dimethylformamide. Synthesis. 1973, 1973, 361–362. DOI: 10.1055/s-1973-22217.
  • Rasheed, S.; Rao, D. N.; Reddy, A. S.; Shankar, R.; Das, P. RSC Adv. 2015, 5, 105607–110574.
  • Chen, C.; Tan, L.; Zhou, P. Approach for the Synthesis of N-Phenylamides from β-Ketobutylanilides Using Dimethylformamide and Dimethylacetamide as the Acyl Donors. J. Saudi Chem. Soc 2015, 19, 327–333. DOI: 10.1016/j.jscs.2014.05.005.
  • Zhang, Q.; Chen, C. J. Direct Acylation of Aryl Amines Using Dimethylformamide and Dimethylacetamide as the Acyl Resources. Saudi Chem. Soc. 2016, 20, 114–119. DOI: 10.1016/j.jscs.2014.09.006.
  • Yang, Y.; Li, Y.; Zhang, Z.; Zhao, Y.; Feng, W. Metal-Free N-Formylation of 2-Aminophenols Using Dimethylformamide and CSA. Synthetic. Comm. 2019, 49, 1040–1046. DOI: 10.1080/00397911.2019.1584319.
  • Glennon, R. A.; Naiman, N. A.; Pierson, M. E.; Smith, J. D.; Ismaiel, A. M.; Titeler, M.; Lyon, R. A. N-(Phthalimidoalkyl) Derivatives of Serotonergic Agents: A Common Interaction at 5-HT1A Serotonin Binding Sites? J. Med. Chem. 1989, 32, 1921–1926. DOI: 10.1021/jm00128a039.
  • Ghaderi, H.; Zolfigol, M. A.; Bayat, Y.; Zarei, M.; Noroozizadeh, E. Syntlett. 2016, 27, 2246–2250.
  • Fuentes-Aguilar, A.; Romero-Hernández, L. L.; Arenas-González, A.; Merino-Montiel, P.; Montiel-Smith, S.; Meza-Reyes, S.; Vega-Báez, J. L.; Plata, G. B.; Padrón, J. M.; López-López, Ó.; Fernández-Bolaños, J. G. New Selenosteroids as Antiproliferative Agents. Org. Biomol. Chem. 2017, 15, 5041–5054. DOI: 10.1039/c7ob00458c.
  • Zhang, L.; Addla, D.; Ponmani, J.; Wang, A.; Xie, D.; Wang, Y.-N.; Zhang, S.-L.; Geng, R.-X.; Cai, G.-X.; Li, S.; Zhou, C.-H. Discovery of Membrane Active Benzimidazole Quinolones-Based Topoisomerase Inhibitors as Potential DNA-Binding Antimicrobial Agents. Eur. J. Med. Chem. 2016, 111, 160–182. DOI: 10.1016/j.ejmech.2016.01.052.
  • Deng, D.; Cui, Y.; Chen, D.; Ai, N. Solubility of CO2 in Amide-Based Brønsted Acidic Ionic Liquids. J. Chem. Themodynamics. 2013, 57, 355–359. DOI: 10.1016/j.jct.2012.09.023.
  • Garner, C. M.; Prince, M. E. An Improved Synthesis of Tetramethylcyclopentadiene. Tetrahedron. Lett. 1994, 35, 2463–2464. DOI: 10.1016/S0040-4039(00)77144-9.
  • Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Stereocontrolled Formation of Cis and Trans Ring Junctions in Hydrindane and Decalin Systems by Palladium-Catalyzed Regioselective and Stereospecific Hydrogenolysis of Allylic Formates. J. Org. Chem. 1992, 57, 1326–1327. DOI: 10.1021/jo00031a005.
  • Caputo, R.; Ferreri, C.; Palumbo, G. Polymer-Supported Phosphine-Halogen Complexes 4 1. Improved Formylation of Alcohols with Dimethylformamide. Synthetic. Comm. 1987, 17, 1629–1636. DOI: 10.1080/00397918708057794.

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