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Mendeleev Communications, 2013, Volume 23, Issue 1, Pages 22–23
DOI: https://doi.org/10.1016/j.mencom.2013.01.007
(Mi mendc2599)
 

This article is cited in 13 scientific papers (total in 13 papers)

The Cyclopropyliminium Rearrangement of Cyclopropylthiazoles

Yu. V. Tomilov, R. F. Salikov, D. N. Platonov, D. L. Lipilin, A. E. Frumkin

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: 2-Cyclopropylthiazole hydrobromides undergo iminocyclopropane-pyrroline rearrangement in a melt to give the corresponding fused heterocycles, viz. 6,7-dihydro-5H-pyrrolo[2,1-b]thiazol-4-ium bromides. 2-Alkyl- and 2-aryl-4-cyclopropylthiazoles transform into analogous fused heterocycles as hydroiodides and noticeably longer.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (148.4 Kb)


Citation: Yu. V. Tomilov, R. F. Salikov, D. N. Platonov, D. L. Lipilin, A. E. Frumkin, “The Cyclopropyliminium Rearrangement of Cyclopropylthiazoles”, Mendeleev Commun., 23:1 (2013), 22–23
Linking options:
  • https://www.mathnet.ru/eng/mendc2599
  • https://www.mathnet.ru/eng/mendc/v23/i1/p22
  • This publication is cited in the following 13 articles:
    1. Efraím Reyes, Liher Prieto, Rubén Manzano, Luisa Carrillo, Uxue Uria, Jose L. Vicario, Organic Reactions, 2024, 1  crossref
    2. Usman Nazeer, Aqsa Mushtaq, Ameer Fawad Zahoor, Freeha Hafeez, Irum Shahzadi, Rabia Akhtar, “Cloke–Wilson rearrangement: a unique gateway to access five-membered heterocycles”, RSC Adv., 13:50 (2023), 35695  crossref
    3. Peter Wipf, Adam P. Montoya, Matthew G. LaPorte, “Synthesis of Benzo[d]pyrrolo[1,2-a]imidazoles by Iminocyclopropane Rearrangement of C-Cyclopropylbenzimidazoles”, HETEROCYCLES, 105:1 (2022), 358  crossref
    4. Yang Xu, Min Wang, Donghui Wei, Rongqiang Tian, Zheng Duan, François Mathey, “An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins”, Dalton Trans., 48:17 (2019), 5523  crossref
    5. Xiaoying Huang, Hui Chen, Zhongzhi Huang, Yanli Xu, Fangyao Li, Xianli Ma, Yanyan Chen, “Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes”, J. Org. Chem., 84:23 (2019), 15283  crossref
    6. Rinat F. Salikov, Konstantin P. Trainov, Anastasia A. Levina, Irina K. Belousova, Michael G. Medvedev, Yury V. Tomilov, “Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement”, J. Org. Chem., 82:1 (2017), 790  crossref
    7. Alexander V. Samet, Evgenia A. Silyanova, Marina N. Semenova, Valentina A. Karnoukhova, Victor V. Semenov, “An Efficient Synthesis of Fused 2‐Aryliminothiazolines via a Solvent‐Free Cyclopropyliminium Rearrangement”, ChemistrySelect, 1:10 (2016), 2373  crossref
    8. Rinat F. Salikov, Aleksandr Yu. Belyy, Nailya S. Khusnutdinova, Yulia V. Vakhitova, Yury V. Tomilov, “Synthesis and cytotoxic properties of tryptamine derivatives”, Bioorganic & Medicinal Chemistry Letters, 25:17 (2015), 3597  crossref
    9. Hisanori Nambu, Masahiro Fukumoto, Wataru Hirota, Takayuki Yakura, “Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes with Amines: Rapid Access to 2-Substituted 4-Hydroxyindole”, Org. Lett., 16:15 (2014), 4012  crossref
    10. R. F. Salikov, D. N. Platonov, D. L. Lipilin, A. E. Frumkin, Yu. V. Tomilov, “The cyclopropyliminium rearrangement of 2-cyclopropyl-4-nitrobenzimidazoles”, Russ Chem Bull, 63:3 (2014), 765  crossref
    11. Rinat F. Salikov, Aleksandr Yu. Belyy, Yury V. Tomilov, “The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines”, Tetrahedron Letters, 55:43 (2014), 5936  crossref
    12. Yury V. Tomilov, Rinat F. Salikov, Dmitry N. Platonov, Dmitry L. Lipilin, Aleksandr E. Frumkin, “ChemInform Abstract: The Cyclopropyliminium Rearrangement of Cyclopropylthiazoles.”, ChemInform, 44:21 (2013)  crossref
    13. Rinat F. Salikov, Dmitry N. Platonov, Aleksandr E. Frumkin, Dmitry L. Lipilin, Yury V. Tomilov, “Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles”, Tetrahedron, 69:16 (2013), 3495  crossref
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