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Mendeleev Communications, 2013, Volume 23, Issue 5, Pages 271–273
DOI: https://doi.org/10.1016/j.mencom.2013.09.011
(Mi mendc2686)
 

This article is cited in 25 scientific papers (total in 25 papers)

Communications

Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone

M. I. Pleshcheva, V. V. Kachalaa, A. S. Goloveshkinb, I. S. Bushmarinovb, V. V. Kuznetsova, D. V. Khakimova, N. N. Makhovaa

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
Abstract: The [3 + 2] cycloaddition of azomethine imines derived from 6-aryl-1,5-diazabicyclo[3.1.0]hexanes to acrylonitrile and 4-nitrophenyl vinyl sulfone proceeds with high diastereoselectivity, but with opposite regioselectivity, which has been clarified by quantum chemical calculations.
Document Type: Article
Language: English


Citation: M. I. Pleshchev, V. V. Kachala, A. S. Goloveshkin, I. S. Bushmarinov, V. V. Kuznetsov, D. V. Khakimov, N. N. Makhova, “Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone”, Mendeleev Commun., 23:5 (2013), 271–273
Linking options:
  • https://www.mathnet.ru/eng/mendc2686
  • https://www.mathnet.ru/eng/mendc/v23/i5/p271
  • This publication is cited in the following 25 articles:
    1. Benedikt W. Grau, Praveen Kumar, Aaron Nilsen, Sanjay V. Malhotra, “Nitrogen-bridgehead compounds: overview, synthesis, and outlook on applications”, Org. Biomol. Chem., 2025  crossref
    2. Ying Hu, Heng-Bin Yu, Yin Tian, Ming-Sheng Xie, Hai-Ming Guo, “Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes”, Org. Lett., 2025  crossref
    3. Heng‐Xian He, Feng Wu, Xu Zhang, Jian‐Jun Feng, “Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C-C/C-N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines”, Angew Chem Int Ed, 2024  crossref
    4. K.O. Marichev, M.P. Doyle, Comprehensive Chirality, 2024, 247  crossref
    5. Swati Samantaray, Prabhat Kumar Maharana, Subhradeep Kar, Sharajit Saha, Tharmalingam Punniyamurthy, “Redox-neutral zinc-catalyzed cascade [1,4]-H shift/annulation of diaziridines with donor–acceptor aziridines”, Chem. Commun., 60:25 (2024), 3441  crossref
    6. Heng‐Xian He, Feng Wu, Xu Zhang, Jian‐Jun Feng, “Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C-C/C-N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines”, Angewandte Chemie, 2024  crossref
    7. Pallab Karjee, Santu Mandal, Bijoy Debnath, Nirali Namdev, Tharmalingam Punniyamurthy, “Expedient (3+3)-annulation of in situ generated azaoxyallyl cations with diaziridines”, Chem. Commun., 59:53 (2023), 8270  crossref
    8. “One-Step Synthesis of 1,3,4-Oxadiazines, 4,5,6,7-Tetrahydro-1h-Indoles, and Functionalized Benzo[B]Carbazoles Catalyzed by Rare Earth Metal Triflates and Cooperative Enamine-Bronsted Acid”, 2023  crossref
    9. Sundaresan Ravindra, C. P. Irfana Jesin, Arivalagan Shabashini, Ganesh Chandra Nandi, “Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines”, Adv Synth Catal, 363:7 (2021), 1756  crossref
    10. Zetryana Puteri Tachrim, Lei Wang, Yuta Murai, Makoto Hashimoto, “New Trends in Diaziridine Formation and Transformation (a Review)”, Molecules, 26:15 (2021), 4496  crossref
    11. Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo, “Sc(OTf)3-Catalyzed Formal [3 + 3] Cycloaddition Reaction of Diaziridines and Quinones for the Synthesis of Benzo[e][1,3,4]oxadiazines”, Org. Lett., 23:8 (2021), 3136  crossref
    12. Uroš Grošelj, Jurij Svete, Jeffery Aubé, Organic Reactions, 2020, 529  crossref
    13. Tanumay Sarkar, Kangkan Talukdar, Subhasish Roy, Tharmalingam Punniyamurthy, “Expedient iron-catalyzed stereospecific synthesis of triazinesviacycloaddition of aziridines with diaziridines”, Chem. Commun., 56:23 (2020), 3381  crossref
    14. N. N. Makhova, L. I. Belen'kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, “Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems”, Russian Chem. Reviews, 89:1 (2020), 55–124  mathnet  mathnet  crossref  isi  scopus
    15. Haifeng Zheng, Michael P. Doyle, “Catalytic Desymmetric Cycloaddition of Diaziridines with Metalloenolcarbenes: The Role of Donor–Acceptor Cyclopropenes”, Angew Chem Int Ed, 58:36 (2019), 12502  crossref
    16. Haifeng Zheng, Michael P. Doyle, “Catalytic Desymmetric Cycloaddition of Diaziridines with Metalloenolcarbenes: The Role of Donor–Acceptor Cyclopropenes”, Angewandte Chemie, 131:36 (2019), 12632  crossref
    17. Nataliya P. Belskaya, Vasiliy A. Bakulev, Zhijin Fan, “Synthesis and (3+2) cycloaddition reactions of N,N ʹ- and C,N-cyclic azomethine imines”, Chem Heterocycl Comp, 52:9 (2016), 627  crossref
    18. Gang Nie, Xiaocong Deng, Xue Lei, Qinquan Hu, Yunfeng Chen, “Mn(iii)-mediated regioselective synthesis of (E)-vinyl sulfones from sodium sulfinates and nitro-olefins”, RSC Adv., 6:79 (2016), 75277  crossref
    19. Carmen Nájera, José M. Sansano, Miguel Yus, “1,3-Dipolar cycloadditions of azomethine imines”, Org. Biomol. Chem., 13:32 (2015), 8596  crossref
    20. Mikhail I. Pleshchev, Nikita V. Das Gupta, Vladimir V. Kuznetsov, Ivan V. Fedyanin, Vadim V. Kachala, Nina N. Makhova, “CAN-mediated new, regioselective one-pot access to bicyclic cationic structures with 2,3-dihydro-1H-pyrazolo[1,2-a]pyrazol-4-ium core”, Tetrahedron, 71:47 (2015), 9012  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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