One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

Diego Carnaroglio, Katia Martina, Giovanni Palmisano, Andrea Penoni, Claudia Domini and Giancarlo Cravotto
Beilstein J. Org. Chem. 2013, 9, 2378–2386.

Supporting Information

Supporting Information File 1: Detailed analytical data of the prepared compounds and a collection of NMR spectra.
Format: PDF Size: 2.2 MB Download

Cite the Following Article

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction
Diego Carnaroglio, Katia Martina, Giovanni Palmisano, Andrea Penoni, Claudia Domini and Giancarlo Cravotto
Beilstein J. Org. Chem. 2013, 9, 2378–2386.

How to Cite

Carnaroglio, D.; Martina, K.; Palmisano, G.; Penoni, A.; Domini, C.; Cravotto, G. Beilstein J. Org. Chem. 2013, 9, 2378–2386. doi:10.3762/bjoc.9.274

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.

Citations to This Article

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

Scholarly Works

  • Chang, W.-J.; Liew, S. Y.; Tan, S.-P. Synthesis of N,N-diethylaminopropylurea and Monosubstituted Urea Derivatives from Primary Amines and Potassium Cyanate. Letters in Organic Chemistry 2023, 20, 877–882. doi:10.2174/1570178620666230330083659
  • Kassie, A. A.; Castro De la Torre, I. Y.; Remy, M. S.; Mukhopadhyay, S.; Kampf, J.; Qu, F.; Sanford, M. S. Metal Identity Effects in the Pincer Complex-Catalyzed Dehydrogenative Coupling of Formamides with Alcohols to Form Carbamates. Organometallics 2023, 42, 1030–1036. doi:10.1021/acs.organomet.3c00175
  • Labiche, A.; Norlöff, M.; Feuillastre, S.; Taran, F.; Audisio, D. Continuous Flow Synthesis of Non‐Symmetrical Ureas from CO2. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202200640
  • Jadhav, K. A.; Itage, S. V.; Bhosle, S. D.; Bhosale, R. S.; Yadav, J. S. Zinc Promoted Urea Synthesis Using Carbonyldiimidazole as Carbonyl Source and Its Application for the Synthesis of Cariprazine. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202201169
  • Webster, C. S.; Balduzzi, F.; Davis, A. P. Tricyclic octaurea "Temples" for the recognition of polar molecules in water. Organic & biomolecular chemistry 2023, 21, 525–532. doi:10.1039/d2ob02061k
  • Asghar, F.; Shakoor, B.; Murtaza, B.; Butler, I. S. An insight on the different synthetic routes for the facile synthesis of O/S-donor carbamide/thiocarbamide analogs and their miscellaneous pharmacodynamic applications. Journal of Sulfur Chemistry 2022, 44, 90–147. doi:10.1080/17415993.2022.2119085
  • Holmin, G. P.; Hood, J. C.; Scanlon, N.; Klumpp, D. A. Phosphonium-carbenium and oxophosphonium-carbenium dications in Friedel-Crafts reactions. Tetrahedron 2022, 121, 132928. doi:10.1016/j.tet.2022.132928
  • Ohata, J.; Uzoewulu, C. P. Translation of a Phosphine- and Azide-Based Reaction to Chemical Modification of Biomolecules in Ionic Liquid. Synlett 2022, 33, 1879–1883. doi:10.1055/a-1908-2066
  • Wen, W.; Cao, H.; Xu, Y.; Ren, Y.; Rao, L.; Shao, X.; Chen, H.; Wu, L.; Liu, J.; Su, C.; Peng, C.; Huang, Y.; Wan, J. N-Acylamino Saccharin as an Emerging Cysteine-Directed Covalent Warhead and Its Application in the Identification of Novel FBPase Inhibitors toward Glucose Reduction. Journal of medicinal chemistry 2022, 65, 9126–9143. doi:10.1021/acs.jmedchem.2c00336
  • Santana, J. S.; Cardoso, E. S.; Triboni, E. R.; Politi, M. J. Polyureas Versatile Polymers for New Academic and Technological Applications. Polymers 2021, 13, 4393. doi:10.3390/polym13244393
  • Huke, C. D.; Taylor, L. J.; Argent, S. P.; Kays, D. L. Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions. ACS Sustainable Chemistry & Engineering 2021, 9, 10704–10709. doi:10.1021/acssuschemeng.1c02907
  • Ronchetti, R.; Moroni, G.; Carotti, A.; Gioiello, A.; Camaioni, E. Recent advances in urea- and thiourea-containing compounds: focus on innovative approaches in medicinal chemistry and organic synthesis. RSC medicinal chemistry 2021, 12, 1046–1064. doi:10.1039/d1md00058f
  • Matinkhoo, K.; Wong, A. A. W. L.; Hambira, C. M.; Kato, B.; Wei, C.; Müller, C.; Hechler, T.; Braun, A.; Gallo, F.; Pahl, A.; Perrin, D. M. Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 10282–10292. doi:10.1002/chem.202101373
  • Kennedy-Ellis, J. J.; Boldt, E. D.; Chemler, S. R. Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes. Organic letters 2020, 22, 8365–8369. doi:10.1021/acs.orglett.0c02988
  • Davies, J. A.; Bull, F. M.; Walker, P. D.; Weir, A. N. M.; Lavigne, R.; Masschelein, J.; Simpson, T. J.; Race, P. R.; Crump, M. P.; Willis, C. L. Total Synthesis of Kalimantacin A. Organic letters 2020, 22, 6349–6353. doi:10.1021/acs.orglett.0c02190
  • Hai, T. A. P.; De Backer, L. J.; Cosford, N. D. P.; Burkart, M. D. Preparation of Mono- and Diisocyanates in Flow from Renewable Carboxylic Acids. Organic Process Research & Development 2020, 24, 2342–2346. doi:10.1021/acs.oprd.0c00167
  • Luchowska-Stańska, U.; Morgan, D.; Yarwood, S. J.; Barker, G. Selective small-molecule EPAC activators. Biochemical Society transactions 2019, 47, 1415–1427. doi:10.1042/bst20190254
  • Gómez, A. M.; Lopez, J. C. Carbohydrates and BODIPYs: access to bioconjugatable and water-soluble BODIPYs. Pure and Applied Chemistry 2019, 91, 1073–1083. doi:10.1515/pac-2019-0204
  • Patil, M.; Poyil, A. N.; Joshi, S. D.; Patil, S. A.; Patil, S. A.; Bugarin, A. Synthesis, molecular docking studies, and antimicrobial evaluation of new structurally diverse ureas. Bioorganic chemistry 2019, 87, 302–311. doi:10.1016/j.bioorg.2019.03.024
  • Selvaraj, V.; Rhagavarshini, T. R.; Krishnadevi, K. An escalation of anticorrosion and microelectrical properties of polyurethane nanocomposites from green Brassica nigra oil. Polymer Bulletin 2018, 76, 469–494. doi:10.1007/s00289-018-2337-7
Other Beilstein-Institut Open Science Activities