Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

Scholarly Works

• Li, Y.; Du, F.-H.; Li, J.; Xu, J.; Yang, Z.; Li, S.; Zhang, C.; Du, Y. Preparation of benziodazole-triflate and its application as both 2-iodobenzamido- and triflate-transfer reagents. Chinese Chemical Letters 2024, 110338. doi:10.1016/j.cclet.2024.110338
• Charushin, V. N.; Verbitskiy, E. V.; Chupakhin, O. N.; Vorobyeva, D. V.; Gribanov, P. S.; Osipov, S. N.; Ivanov, A. V.; Martynovskaya, S. V.; Sagitova, E. F.; Dyachenko, V. D.; Dyachenko, I. V.; Krivokolylsko, S. G.; Dotsenko, V. V.; Aksenov, A. V.; Aksenov, D. A.; Aksenov, N. A.; Larin, A. A.; Fershtat, L. L.; Muzalevskiy, V. M.; Nenajdenko, V. G.; Gulevskaya, A. V.; Pozharskii, A. F.; Filatova, E. A.; Belyaeva, K. V.; Trofimov, B. A.; Balova, I. A.; Danilkina, N. A.; Govdi, A. I.; Tikhomirov, A. S.; Shchekotikhin, A. E.; Novikov, M. S.; Rostovskii, N. V.; Khlebnikov, A. F.; Klimochkin, Y. N.; Leonova, M. V.; Tkachenko, I. M.; Mamedov, V. A. O.; Mamedova, V. L.; Zhukova, N. A.; Semenov, V. E.; Sinyashin, O. G.; Borshchev, O. V.; Luponosov, Y. N.; Ponomarenko, S. A.; Fisyuk, A. S.; Kostyuchenko, A. S.; Ilkin, V. G.; Beryozkina, T. V.; Bakulev, V. A.; Gazizov, A. S.; Zagidullin, A. A.; Karasik, A. A.; Kukushkin, M. E.; Beloglazkina, E. K.; Golantsov, N. E.; Festa, A. A.; Voskresenskii, L. G.; Moshkin, V. S.; Buev, E. M.; Sosnovskikh, V. Y.; Mironova, I. A.; Postnikov, P. S.; Zhdankin, V. V.; Yusubov, M. S. O.; Yaremenko, I. A.; Vil', V. A.; Krylov, I. B.; Terent'ev, A. O.; Gorbunova, Y. G.; Martynov, A. G.; Tsivadze, A. Y.; Stuzhin, P. A.; Ivanova, S. S.; Koifman, O. I.; Burov, O. N.; Kletskii, M. E.; Kurbatov, S. V.; Yarovaya, O. I.; Volcho, K. P.; Salakhutdinov, N. F.; Panova, M. A.; Burgart, Y. V.; Saloutin, V. I.; Sitdikova, A. R.; Shchegravina, E. S.; Fedorov, A. Y. The chemistry of heterocycles in the 21st century. Russian Chemical Reviews 2024, 93, RCR5125. doi:10.59761/rcr5125
• Uehara, D.; Adachi, S.; Tsubouchi, A.; Okada, Y.; Zhdankin, V. V.; Yoshimura, A.; Saito, A. Peptide coupling using recyclable bicyclic benziodazolone. Chemical communications (Cambridge, England) 2024, 60, 956–959. doi:10.1039/d3cc04431a
• Sihag, M.; Soni, R.; Rani, N.; Kinger, M.; Kumar Aneja, D. Recent Synthetic Applications of Hypervalent Iodine Reagents. A Review in Three Installments: Installment I. Organic Preparations and Procedures International 2022, 55, 1–62. doi:10.1080/00304948.2022.2113964
• Zhang, Y.; Long, Z.; Yan, L.; Liu, L.; Yang, L.; Le, Y. Discovery of 4-nitro-3-phenylisoxazole derivatives as potent antibacterial agents derived from the studies of [3 + 2] cycloaddition. RSC advances 2022, 12, 25633–25638. doi:10.1039/d2ra05009a
• Shea, M. T.; Rohde, G. T.; Vlasenko, Y. A.; Postnikov, P. S.; Yusubov, M. S.; Zhdankin, V. V.; Saito, A.; Yoshimura, A. Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines. Molecules (Basel, Switzerland) 2021, 26, 7355. doi:10.3390/molecules26237355
• Boelke, A.; Sadat, S.; Lork, E.; Nachtsheim, B. J. Pseudocyclic bis-N-heterocycle-stabilized iodanes - synthesis, characterization and applications. Chemical communications (Cambridge, England) 2021, 57, 7434–7437. doi:10.1039/d1cc03097c
• Le Du, E.; Duhail, T.; Wodrich, M. D.; Scopelliti, R.; Fadaei-Tirani, F.; Anselmi, E.; Magnier, E.; Waser, J. Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 10979–10986. doi:10.1002/chem.202101475
• Vlasenko, Y. А.; Yusubov, M. S.; Shafir, A.; Postnikov, P. S. Hypervalent iodine in the structure of N-heterocycles: synthesis, structure, and application in organic synthesis. Chemistry of Heterocyclic Compounds 2020, 56, 854–866. doi:10.1007/s10593-020-02742-0
• Li, Q.; Zhuang, C.; Wang, D.; Zhang, W.; Jia, R.; Sun, F.; Zhang, Y.; Du, Y. Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A. Beilstein journal of organic chemistry 2019, 15, 2958–2965. doi:10.3762/bjoc.15.291
• Zhang, G.; Wang, Y.; Xu, J.; Sun, J.; Sun, F.; Zhang, Y.; Zhang, C.; Du, Y. A new hypervalent iodine(III/V) oxidant and its application to the synthesis of 2H-azirines. Chemical science 2019, 11, 947–953. doi:10.1039/c9sc05536c
• Hari, D. P.; Schouwey, L.; Barber, V.; Scopelliti, R.; Fadaei-Tirani, F.; Waser, J. Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 9522–9528. doi:10.1002/chem.201900950
• Vlasenko, Y. A.; Postnikov, P. S.; Trusova, M. E.; Shafir, A.; Zhdankin, V. V.; Yoshimura, A.; Yusubov, M. S. Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts. The Journal of organic chemistry 2018, 83, 12056–12070. doi:10.1021/acs.joc.8b01995

Explore citations to this article at