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Mendeleev Communications, 2013, Volume 23, Issue 3, Pages 140–141
DOI: https://doi.org/10.1016/j.mencom.2013.05.006
(Mi mendc2640)
 

This article is cited in 12 scientific papers (total in 12 papers)

Communications

Synthesis of 6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines and 5-(arylmethylidene)hexahydropyrrolo[1,2-a]imidazoles by the interaction of alk-4-ynals with a,?-diaminoalkanes in DMSO in the presence of KOH

K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Cyclization of alk-4-ynals with a,?-diaminoalkanes in DMSO under the action of KOH affords bicyclic N,N-enaminals – 6-(aryl- methylidene)octahydro[1,2-a]pyrimidines and 5-(arylmethylidene)hexahydro[1,2-a]imidazoles.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (240.9 Kb)


Citation: K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of 6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines and 5-(arylmethylidene)hexahydropyrrolo[1,2-a]imidazoles by the interaction of alk-4-ynals with a,?-diaminoalkanes in DMSO in the presence of KOH”, Mendeleev Commun., 23:3 (2013), 140–141
Linking options:
  • https://www.mathnet.ru/eng/mendc2640
  • https://www.mathnet.ru/eng/mendc/v23/i3/p140
  • This publication is cited in the following 12 articles:
    1. Jean Suffert, Comprehensive Heterocyclic Chemistry IV, 2022, 38  crossref
    2. Lesya M. Saliyeva, Irina V. Dyachenko, Ivanna Yu. Danyliuk, Mykhailo V. Vovk, “Di-, tetra-, and perhydropyrrolo[1,2-a]imidazoles: The Methods of Synthesis and Some Aspects of Application”, Chem Heterocycl Comp, 58:12 (2022), 661  crossref
    3. Yu. V. Tomilov, L. G. Menchikov, E. A. Shapiro, V. D. Gvozdev, K. N. Shavrin, N. V. Volchkov, M. B. Lipkind, M. P. Egorov, S. E. Boganov, V. N. Khabashesku, E. G. Baskir, “Carbenes, related intermediates, and small-sized cycles: contribution from Professor Nefedov's laboratory”, Mendeleev Commun., 31:6 (2021), 750–768  mathnet  crossref
    4. V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “New selective cyclizations of alk-4-ynals with primary amines and azoles:one-pot synthesis of 2-azolylpyrrolidines and 3-iminocyclopentenes”, Mendeleev Commun., 28:2 (2018), 123–125  mathnet  crossref
    5. V. D. Gvozdev, K. N. Shavrin, E. G. Baskir, M. P. Egorov, O. M. Nefedov, “Selective one-pot synthesis of 11-arylmethylidene-11H-isoindolo-[2,1-a]benzimidazoles and 6-arylbenzimidazo[2,1-a]isoquinolines from o-alkynylbenzaldehydes and o-diaminobenzenes”, Mendeleev Commun., 27:3 (2017), 231–233  mathnet  crossref
    6. V. D. Gvozdev, K. N. Shavrin, E. G. Baskir, M. P. Egorov, O. M. Nefedov, “Cyclization of alk-4-ynals with o-diaminoarenes as a selective one-pot synthesis of arylmethylidene-substituted 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles and 7,8-dihydro-6H-pyrrolo[1',2':1,2]imidazo[4,5-b]pyridines”, Russ Chem Bull, 65:7 (2016), 1829  crossref
    7. V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene”, Mendeleev Commun., 26:1 (2016), 3–5  mathnet  crossref
    8. V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine”, Mendeleev Commun., 25:5 (2015), 329–331  mathnet  crossref
    9. V. D. Gvozdev, K. N. Shavrin, O. M. Nefedov, “A new synthesis of bicyclic N,O- and N,S-enaminals by the anionic cyclization of alk-4-ynals with amino alcohols and amino thiols”, Russ Chem Bull, 63:2 (2014), 409  crossref
    10. B. A. Trofimov, E. Yu. Schmidt, “Reactions of acetylenes in superbasic media. Recent advances”, Russian Chem. Reviews, 83:7 (2014), 600–619  mathnet  mathnet  crossref  isi  scopus
    11. Konstantin N. Shavrin, Valentin D. Gvozdev, Oleg M. Nefedov, “ChemInform Abstract: Synthesis of 6‐(Arylmethylidene)octahydropyrrolo[1,2‐a]pyrimidines and 5‐(Arylmethylidene)hexahydropyrrolo[1,2‐a]imidazoles by the Interaction of Alk‐4‐ynals with α,ω‐Diaminoalkanes in DMSO in the Presence of KOH.”, ChemInform, 44:44 (2013)  crossref
    12. V. D. Gvozdev, K. N. Shavrin, O. M. Nefedov, “Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH”, Russ Chem Bull, 62:11 (2013), 2430  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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