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Mendeleev Communications, 2015, Volume 25, Issue 3, Pages 188–190
DOI: https://doi.org/10.1016/j.mencom.2015.05.009
(Mi mendc2345)
 

This article is cited in 15 scientific papers (total in 15 papers)

Communications

Regio- and stereoselective cycloaddition of stable azomethine imines to (arylmethylidene)malononitriles

M. I. Pleshcheva, N. V. Das Guptaa, M. I. Struchkovaa, A. S. Goloveshkinb, I. S. Bushmarinovb, 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: [3 + 2] Cycloaddition of 1-arylmethylidene-3-oxopyrazolidin-1-ium-2-ides (stable azomethine imines) to (arylmethylidene)malononitriles proceeds regio- and stereoselectively to afford 1,3-diaryl-5-oxotetrahydropyrazolo[1,2-a]pyrazole-2-carbonitriles that proved resistant to azomethine imines metathesis.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (238.4 Kb)


Citation: M. I. Pleshchev, N. V. Das Gupta, M. I. Struchkova, A. S. Goloveshkin, I. S. Bushmarinov, D. V. Khakimov, N. N. Makhova, “Regio- and stereoselective cycloaddition of stable azomethine imines to (arylmethylidene)malononitriles”, Mendeleev Commun., 25:3 (2015), 188–190
Linking options:
  • https://www.mathnet.ru/eng/mendc2345
  • https://www.mathnet.ru/eng/mendc/v25/i3/p188
  • This publication is cited in the following 15 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. Ramaraj Selvaraj, Govinda Rajulu G., Karthikeyan Soundararajan, Shekhar M. S, Akshatha K. P., Palani S. Subramanian, Saravanan Subramanian, Sandeep S., Rajendran Arunachalam, “Lanthanide One‐Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of N,N'‐Bicyclic Pyrazolidine Scaffolds”, Adv Synth Catal, 2025  crossref
    4. 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
    5. Emmanuel R. Buabeng, Md Shamim, Maged Henary, Comprehensive Heterocyclic Chemistry IV, 2022, 311  crossref
    6. Haipeng Hu, Jinxiu Xu, Fang Wang, Shunxi Dong, Xiaohua Liu, Xiaoming Feng, “Chiral ScIII–N,N′-Dioxide-Catalyzed 1,3-Dipolar Cycloaddition of Diaziridines with Chalcones”, Org. Lett., 22:1 (2020), 93  crossref
    7. F. Matloubi Moghaddam, M. Eslami, A. Siahpoosh, G. Hoda, “Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold via C-3 umpolung of isatin N,N′-cyclic azomethine imine”, New J. Chem., 43:26 (2019), 10318  crossref
    8. Alexey O. Chagarovskiy, Vladimir S. Vasin, Vladimir V. Kuznetsov, Olga A. Ivanova, Victor B. Rybakov, Alexey N. Shumsky, Nina N. Makhova, Igor V. Trushkov, “(3+3)‐Annulation of Donor–Acceptor Cyclopropanes with Diaziridines”, Angewandte Chemie, 130:32 (2018), 10495  crossref
    9. Mar Ríos‐Gutiérrez, Lilia Nasri, Abdelmalek Khorief Nacereddine, Abdelhafid Djerourou, Luis R. Domingo, “A molecular electron density theory study of the [3 + 2] cycloaddition reaction between an azomethine imine and electron deficient ethylenes”, J of Physical Organic Chem, 31:6 (2018)  crossref
    10. Jovana P. Jovanović, Sladjana B. Novaković, Goran A. Bogdanović, Aleksandra Minić, Anka Pejović, Jelena Katanić, Vladimir Mihailović, Branislav Nastasijević, Dragana Stevanović, Ivan Damljanović, “Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′-Cyclic azomethine imines”, Journal of Organometallic Chemistry, 860 (2018), 85  crossref
    11. Alexey O. Chagarovskiy, Vladimir S. Vasin, Vladimir V. Kuznetsov, Olga A. Ivanova, Victor B. Rybakov, Alexey N. Shumsky, Nina N. Makhova, Igor V. Trushkov, “(3+3)‐Annulation of Donor–Acceptor Cyclopropanes with Diaziridines”, Angew Chem Int Ed, 57:32 (2018), 10338  crossref
    12. Hong-Wu Zhao, Bo Li, Hai-Liang Pang, Ting Tian, Xiao-Qin Chen, Xiu-Qing Song, Wei Meng, Zhao Yang, Yu-Di Zhao, Yue-Yang Liu, “Diastereoselective 1,3-Dipolar Cycloadditions of N,N′-Cyclic Azomethine Imines with Iminooxindoles for Access to Oxindole Spiro-N,N-bicyclic Heterocycles”, Org. Lett., 18:4 (2016), 848  crossref
    13. 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
    14. Mikhail I. Pleshchev, Nikita V. Das Gupta, Marina I. Struchkova, Alexander S. Goloveshkin, Ivan S. Bushmarinov, Dmitriy V. Khakimov, Nina N. Makhova, “ChemInform Abstract: Regio‐ and Stereoselective Cycloaddition of Stable Azomethine Imines to (Arylmethylidene)malononitriles.”, ChemInform, 46:41 (2015)  crossref
    15. 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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