Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes

Jury J. Medvedev, Ilya V. Efimov, Yuri M. Shafran, Vitaliy V. Suslonov, Vasiliy A. Bakulev and Valerij A. Nikolaev
Beilstein J. Org. Chem. 2017, 13, 2569–2576. https://doi.org/10.3762/bjoc.13.253

Supporting Information

Supporting Information File 1: NMR spectra of all new compounds and data of X-ray analysis.
Format: PDF Size: 8.0 MB Download
Supporting Information File 2: Experimental procedures and characterization data of all new compounds.
Format: PDF Size: 317.5 KB Download

Cite the Following Article

Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes
Jury J. Medvedev, Ilya V. Efimov, Yuri M. Shafran, Vitaliy V. Suslonov, Vasiliy A. Bakulev and Valerij A. Nikolaev
Beilstein J. Org. Chem. 2017, 13, 2569–2576. https://doi.org/10.3762/bjoc.13.253

How to Cite

Medvedev, J. J.; Efimov, I. V.; Shafran, Y. M.; Suslonov, V. V.; Bakulev, V. A.; Nikolaev, V. A. Beilstein J. Org. Chem. 2017, 13, 2569–2576. doi:10.3762/bjoc.13.253

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: 152.5 KB Download

Citations to This Article

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

Scholarly Works

  • Maneesha, M.; Aneeja, T.; Anilkumar, G. Advances and prospects in rhodium catalyzed domino reactions. Journal of Organometallic Chemistry 2024, 1008, 123049. doi:10.1016/j.jorganchem.2024.123049
  • Ilkin, V. G.; Filimonov, V. O.; Seliverstova, E. A.; Novikov, M. S.; Beryozkina, T. V.; Gagarin, A. A.; Belskaya, N. P.; Muthipeedika, N. J.; Bakulev, V. A.; Dehaen, W. Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds. The Journal of organic chemistry 2022, 87, 12196–12213. doi:10.1021/acs.joc.2c01352
  • Zheng, Z.-C.; Yang, C.; Kuang, X.; Ding, C.-H. Comprehensive Heterocyclic Chemistry IV - Thiophenes and Their Benzo Derivatives: Synthesis. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 519–612. doi:10.1016/b978-0-12-409547-2.14932-7
  • Berry, J. F. Comprehensive Coordination Chemistry III - Metal–Metal Bonded Compounds of the Group IX Elements. Comprehensive Coordination Chemistry III; Elsevier, 2021; pp 4–42. doi:10.1016/b978-0-08-102688-5.00103-3
  • Gagarin, A. A.; Suntsova, P. O.; Minin, A. S.; Pozdina, V. A.; Slepukhin, P. A.; Benassi, E.; Belskaya, N. P. Two Approaches for the Synthesis of Fused Dihydropyridines via a 1,6-Electrocyclic Reaction: Fluorescent Properties and Prospects for Application. The Journal of organic chemistry 2020, 85, 13837–13852. doi:10.1021/acs.joc.0c01934
  • Mlostoń, G.; Heimgartner, H. Reactions of thiocarbonyl compounds with electrophilic and nucleophilic carbenes as well as with their metal complexes. Journal of Sulfur Chemistry 2020, 41, 672–700. doi:10.1080/17415993.2020.1780237
  • He, Y.; Lou, J.; Wu, P.; Zhou, Y.-G.; Yu, Z. Copper-Catalyzed Annulative Coupling of S,S-Disubstituted Enones with Diazo Compounds to Access Highly Functionalized Thiophene Derivatives. The Journal of organic chemistry 2020, 85, 1044–1053. doi:10.1021/acs.joc.9b02982
  • Bakulev, V. A.; Shafran, Y.; Dehaen, W. Progress in intermolecular and intramolecular reactions of thioamides with diazo compounds and azides. Tetrahedron Letters 2019, 60, 513–523. doi:10.1016/j.tetlet.2019.01.032
  • Liu, Z.; Wu, P.; He, Y.; Yang, T.; Yu, Z. [4+1] Cycloaddition of Enaminothiones and Aldehyde N‐Tosylhydrazones Toward 3‐Aminothiophenes. Advanced Synthesis & Catalysis 2018, 360, 4381–4392. doi:10.1002/adsc.201801028
  • Konovalov, A. I.; Antipin, I. S.; Burilov, V.; Madzhidov, T. I.; Kurbangalieva, A.; Nemtarev, A. V.; Solovieva, S. E.; Stoikov, I. I.; Mamedov, V. A.; Zakharova, L. Y.; Gavrilova, E. L.; Sinyashin, O. G.; Balova, I. A.; Vasilyev, A. V.; Zenkevich, I. G.; Krasavin, M. Y.; Kuznetsov, M. A.; Molchanov, A. P.; Novikov, M. S.; Nikolaev, V. A.; Rodina, L. L.; Khlebnikov, A. F.; Beletskaya, I. P.; Vatsadze, S. Z.; Gromov, S. P.; Zyk, N. V.; Lebedev, A. T.; Lemenovskii, D. A.; Petrosyan, V. S.; Nenaidenko, V. G.; Negrebetskii, V. V.; Baukov, Y. I.; Shmigol, T. A.; Korlyukov, A. A.; Tikhomirov, A. S.; Shchekotikhin, A. E.; Traven, V. F.; Voskresenskii, L. G.; Zubkov, F. I.; Golubchikov, O. A.; Semeikin, A. S.; Berezin, D. B.; Stuzhin, P. A.; Filimonov, V. D.; Krasnokutskaya, E. A.; Fedorov, A. Y.; Nyuchev, A. V.; Orlov, V. Y.; Begunov, R. S.; Rusakov, A. I.; Kolobov, A. V.; Kofanov, E. R.; Fedotova, O. V.; Egorova, A. Y.; Charushin, V. N.; Chupakhin, O. N.; Klimochkin, Y. N.; Osyanin, V. A.; Reznikov, A. N.; Fisyuk, A. S.; Sagitullina, G. P.; Aksenov, A. V.; Aksenov, N. A.; Grachev, M. K.; Maslennikova, V. I.; Koroteev, M. P.; Brel, A. K.; Lisina, S. V.; Medvedeva, S. M.; Shikhaliev, K. S.; Suboch, G. A.; Tovbis, M. S.; Mironovich, L. M.; Ivanov, S. M.; Kurbatov, S. V.; Kletskii, M. E.; Burov, O. N.; Kobrakov, K. I.; Kuznetsov, D. N. Modern Trends of Organic Chemistry in Russian Universities. Russian Journal of Organic Chemistry 2018, 54, 157–371. doi:10.1134/s107042801802001x
Other Beilstein-Institut Open Science Activities