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Mendeleev Communications, 2015, Volume 25, Issue 5, Pages 329–331
DOI: https://doi.org/10.1016/j.mencom.2015.09.002
(Mi mendc2396)
 

This article is cited in 7 scientific papers (total in 7 papers)

Communications

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

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

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Full-text PDF (248 kB) Citations (7)
Abstract: Cyclization of 5-arylalk-4-ynals with o-aminobenzylamine or o-aminobenzyl alcohol in DMSO under the sequential action of NH4Br and KOH affords (E)-1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazolines or (E)-1-arylmethylidene-1,2,3,3a-tetrahydro- 5H-pyrrolo-[1,2-a][3,1]benzoxazines; the latter without substituents in the 3-position easily isomerize into the corresponding 2-arylmethyl- 1-(2-hydroxymethylphenyl)pyrroles.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (209.7 Kb)


Citation: 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
Linking options:
  • https://www.mathnet.ru/eng/mendc2396
  • https://www.mathnet.ru/eng/mendc/v25/i5/p329
  • This publication is cited in the following 7 articles:
    1. 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
    2. Ke Xiao, Congjun Zhu, Maohua Lin, Chuanjun Song, Junbiao Chang, “Base‐Promoted Cycloisomerization for the Synthesis of Indolizines and Related Heterocycles”, ChemistrySelect, 3:40 (2018), 11270  crossref
    3. 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
    4. 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
    5. Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov, Oleg M. Nefedov, “ChemInform Abstract: 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.”, ChemInform, 47:7 (2016)  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
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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