This article is cited in 18 scientific papers (total in 18 papers)
5-Methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines in the reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes
Abstract:
Unusual reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2-diaminoethane, 1,3-diaminopropane and 1-methylamino-3-aminopropane in THF at 20 °C give previously unknown 5-methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines with up to 60% yields.
Document Type:
Article
Language: English
Citation:
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “5-Methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines in the reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes”, Mendeleev Commun., 18:6 (2008), 300–301
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https://www.mathnet.ru/eng/mendc3334
https://www.mathnet.ru/eng/mendc/v18/i6/p300
This publication is cited in the following 18 articles:
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, “Alkynyl cyclopropanes in organic synthesis”, Russ Chem Bull, 73:1 (2024), 53
Jean Suffert, Comprehensive Heterocyclic Chemistry IV, 2022, 38
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
V. D. Gvozdev, K. N. Shavrin, E. G. Baskir, M. P. Egorov, O. M. Nefedov, “Chloro(4-methylpent-3-en-1-ynyl)carbene: IR spectrum, structure, photochemical transformations, and reactions with alkenes”, Russ Chem Bull, 70:8 (2021), 1575
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Methods for the synthesis of functionalized alkynylcyclopropanes”, Russ Chem Bull, 70:11 (2021), 2051
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
V. D. Gvozdev, K. N. Shavrin, O. M. Nefedov, “Lithiation of 1-alkynyl-1-chlorocyclopropanes and subsequent reactions with electrophilic reagents: synthesis of functionalized alkynyl- and vinylidenecyclopropanes”, Russ Chem Bull, 68:7 (2019), 1384
V. D. Gvozdev, K. N. Shavrin, E. G. Baskir, O. M. Nefedov, M. P. Egorov, “Alkylthio(4-methylpent-3-en-1-ynyl)carbenes: generation by the photolysis of 5-alkylthioethynyl-3,3-dimethyl-3H-pyrazoles and reactions with alkenes”, Mendeleev Commun., 29:2 (2019), 140–142
Vladimir Maslivetc, Colby Barrett, Nicolai A. Aksenov, Marina Rubina, Michael Rubin, “Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes”, Org. Biomol. Chem., 16:2 (2018), 285
Vladimir A. Maslivetc, Danielle N. Turner, Kimberly N. McNair, Liliya Frolova, Snezna Rogelj, Anna A. Maslivetc, Nicolai A. Aksenov, Marina Rubina, Michael Rubin, “Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7-exo-trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity”, J. Org. Chem., 83:10 (2018), 5650
V. D. Gvozdev, K. N. Shavrin, A. A. Ageshina, O. M. Nefedov, “Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents”, Russ Chem Bull, 66:5 (2017), 862
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
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
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
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of 5-methylidenehexahydropyrrolo[l,2-a]imidazoles and 6-methylideneoctahydropyrrolo[l,2-a]pyrimidines by the reaction of 1-alkynyl-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes”, Russ Chem Bull, 59:7 (2010), 1451
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Synthesis of 1-alkynyl-2-dialkylaminocyclopropanes and 1-alkynyl-2-diazolylcyclopropanes by reactions of 1-alkynyl-1-chlorocyclopropanes with amines and their lithium derivatives”, Russ Chem Bull, 59:2 (2010), 396
Konstantin N. Shavrin, Valentin D. Gvozdev, Oleg M. Nefedov, “ChemInform Abstract: 5‐Methylenehexahydropyrrolo[1,2‐a]imidazoles and 6‐Methyleneoctahydropyrrolo[1,2‐a]pyrimidines in the Reactions of 1‐(Alk‐1‐ynyl)‐1‐chlorocyclopropanes with Lithium Derivatives of 1,2‐ and 1,3‐Diaminoalkanes.”, ChemInform, 40:16 (2009)
K. N. Shavrin, V. D. Gvozdev, O. M. Nefedov, “Reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with arenethiols and alkanethiols in dimethyl sulfoxide in the presense of KOH”, Russ Chem Bull, 58:12 (2009), 2432
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