Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

Paola Vitale, Luciana Cicco, Ilaria Cellamare, Filippo M. Perna, Antonio Salomone and Vito Capriati
Beilstein J. Org. Chem. 2020, 16, 1915–1923. https://doi.org/10.3762/bjoc.16.158

Supporting Information

Supporting Information File 1: Compound characterization data and NMR spectra.
Format: PDF Size: 2.4 MB Download

Cite the Following Article

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
Paola Vitale, Luciana Cicco, Ilaria Cellamare, Filippo M. Perna, Antonio Salomone and Vito Capriati
Beilstein J. Org. Chem. 2020, 16, 1915–1923. https://doi.org/10.3762/bjoc.16.158

How to Cite

Vitale, P.; Cicco, L.; Cellamare, I.; Perna, F. M.; Salomone, A.; Capriati, V. Beilstein J. Org. Chem. 2020, 16, 1915–1923. doi:10.3762/bjoc.16.158

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 1.1 MB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Cicco, L.; Perna, F. M.; Capriati, V.; Vitale, P. A Sustainable Synthetic Approach to Tacrine and Cholinesterase Inhibitors in Deep Eutectic Solvents under Aerobic Conditions. Molecules 2024, 29, 1399. doi:10.3390/molecules29061399
  • She, C.; Wang, A.; Liu, S.; Shu, W.; Yu, W. Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis. Chinese Journal of Organic Chemistry 2024, 44, 481. doi:10.6023/cjoc202307009
  • Zlotin, S. G.; Egorova, K. S.; Ananikov, V. P.; Akulov, A. A.; Varaksin, M. V.; Chupakhin, O. N.; Charushin, V. N.; Bryliakov, K. P.; Averin, A. D.; Beletskaya, I. P.; Dolengovski, E. L.; Budnikova, Y. H.; Sinyashin, O. G.; Gafurov, Z. N.; Kantyukov, A. O.; Yakhvarov, D. G.; Aksenov, A. V.; Elinson, M. N.; Nenajdenko, V. G.; Chibiryaev, A. M.; Nesterov, N. S.; Kozlova, E. A.; Martyanov, O. N.; Balova, I. A.; Sorokoumov, V. N.; Guk, D. A.; Beloglazkina, E. K.; Lemenovskii, D. A.; Chukicheva, I. Y.; Frolova, L. L.; Izmest'ev, E. S.; Dvornikova, I. A.; Popov, A. V.; Kutchin, A. V.; Borisova, D. M.; Kalinina, A. A.; Muzafarov, A. M.; Kuchurov, I. V.; Maximov, A. L.; Zolotukhina, A. V. The green chemistry paradigm in modern organic synthesis. Успехи химии 2023, 92. doi:10.59761/rcr5104
  • Perrone, S.; Messa, F.; Troisi, L.; Salomone, A. N-, O- and S-Heterocycles Synthesis in Deep Eutectic Solvents. Molecules (Basel, Switzerland) 2023, 28, 3459. doi:10.3390/molecules28083459
  • Newar, U. D.; Bora, K.; Borra, S.; Maurya, R. A. DBU mediated coupling of isatin with phenacyl azides: synthesis of 2-oxoindolin-3-ylbenzoates. New Journal of Chemistry 2023, 47, 2464–2473. doi:10.1039/d2nj05661e
  • Cicco, L.; Roggio, M.; López-Aguilar, M.; Ramos-Martín, M.; Perna, F. M.; García-Álvarez, J.; Vitale, P.; Capriati, V. Selective Aerobic Oxidation of Alcohols in Low Melting Mixtures and Water and Use for Telescoped One-Pot Hybrid Reactions. ChemistryOpen 2022, 11, e202200160. doi:10.1002/open.202200160
  • Dilauro, G.; Cicco, L.; Vitale, P.; Perna, F. M.; Capriati, V. Ligand‐Free Pd‐Catalyzed Reductive Mizoroki‐Heck Reaction Strategy for the One‐Pot Synthesis of Functionalized Oxygen Heterocycles in Deep Eutectic Solvents. European Journal of Organic Chemistry 2022, 26. doi:10.1002/ejoc.202200814
  • Cicco, L.; Perna, F. M.; Falcicchio, A.; Altomare, A.; Messa, F.; Salomone, A.; Capriati, V.; Vitale, P. 1,3‐Dipolar Cycloaddition of Alkanone Enolates with Azides in Deep Eutectic Solvents for the Metal‐Free Regioselective Synthesis of Densely Functionalized 1,2,3‐Triazoles. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200843
  • Borkotoky, L.; Maurya, R. A. Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200254
  • Quivelli, A. F.; Rossi, F. V.; Vitale, P.; García-Álvarez, J.; Perna, F. M.; Capriati, V. Sustainable and Scalable Two-Step Synthesis of Thenfadil and Some Analogs in Deep Eutectic Solvents: From Laboratory to Industry. ACS Sustainable Chemistry & Engineering 2022, 10, 4065–4072. doi:10.1021/acssuschemeng.2c00417
  • Quivelli, A. F.; Marinò, M.; Vitale, P.; García-Álvarez, J.; Perna, F. M.; Capriati, V. Ligand-free Copper-Catalyzed Ullmann-type C-O Bond Formation in Non-innocent Deep Eutectic Solvents under Aerobic Conditions. ChemSusChem 2021, 15, e202102211. doi:10.1002/cssc.202102211
  • Shaibuna, M.; Kuniyil, M. J. K.; Sreekumar, K. Deep eutectic solvent assisted synthesis of dihydropyrimidinones/thiones via Biginelli reaction: theoretical investigations on their electronic and global reactivity descriptors. New Journal of Chemistry 2021, 45, 20765–20775. doi:10.1039/d1nj03879f
  • Vitale, P.; Cicco, L.; Perna, F. M.; Capriati, V. Introducing deep eutectic solvents in enolate chemistry: synthesis of 1-arylpropan-2-ones under aerobic conditions. Reaction Chemistry & Engineering 2021, 6, 1796–1800. doi:10.1039/d1re00297j
  • Giofrè, S. V.; Tiecco, M.; Ferlazzo, A.; Romeo, R.; Ciancaleoni, G.; Germani, R.; Iannazzo, D. Base-Free Copper-Catalyzed Azide-Alkyne Click Cycloadditions (CuAAc) in Natural Deep Eutectic Solvents as Green and Catalytic Reaction Media**. European Journal of Organic Chemistry 2021, 2021, 4777–4789. doi:10.1002/ejoc.202100698
  • Tiuftiakov, N. Y.; Strelnikova, J. O.; Filippov, I. P.; Khaidarov, A. R.; Khlebnikov, A. F.; Bunev, A. S.; Novikov, M. S.; Rostovskii, N. V. Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement. Organic letters 2021, 23, 6998–7002. doi:10.1021/acs.orglett.1c02706
  • Ríos-Lombardía, N.; Cicco, L.; Yamamoto, K.; Hernández-Fernández, J. A.; Morís, F.; Capriati, V.; García-Álvarez, J.; González-Sabín, J. Deep eutectic solvent-catalyzed Meyer-Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions. Chemical communications (Cambridge, England) 2020, 56, 15165–15168. doi:10.1039/d0cc06584f
Other Beilstein-Institut Open Science Activities