IMIDAZOLIUM YLIDES: CYCLOADDITION versus HYDROLISIS

Authors

  • Dumitrela CUCU Faculty of Chemistry; Interdisciplinary Research Institute - CERNESIM Center, Alexandru Ioan Cuza University, Iasi, Romania. Corresponding author: ionelm@uaic.ro.
  • Violeta MANGALAGIU Interdisciplinary Research Institute - CERNESIM Center, Alexandru Ioan Cuza University, Iasi, Romania. Corresponding author: ionelm@uaic.ro. https://orcid.org/0000-0002-9768-8686
  • Dorina AMARIUCAI-MANTU Faculty of Chemistry, Alexandru Ioan Cuza University, Iasi, Romania. Corresponding author: ionelm@uaic.ro. https://orcid.org/0000-0001-8744-7742
  • Vasilichia ANTOCI Faculty of Chemistry, Alexandru Ioan Cuza University, Iasi, Romania. Corresponding author: ionelm@uaic.ro. https://orcid.org/0000-0003-1013-1293
  • Ionel I. MANGALAGIU Faculty of Chemistry; Interdisciplinary Research Institute - CERNESIM Center, Alexandru Ioan Cuza University, Iasi, Romania. Corresponding author: ionelm@uaic.ro. https://orcid.org/0000-0002-4632-5076

DOI:

https://doi.org/10.24193/subbchem.2019.3.05

Keywords:

imidazolium ylides, hydrolysis, cycloaddition, reaction mechanism, diene, pyrrolo-imidazole derivatives

Abstract

Reactions of imidazolium ylides with dimethyl acetylenedicarboxylate in polar solvents (methanol) were studied. In the competition between cycloaddition versus hydrolysis, the last one prevails leading to base heterocycle, diene structures and benzoate esters. A feasible reaction mechanism is presented. When fused pyrrolo-imidazole derivatives are desirable to be obtained, polar solvents should be avoided.

References

E. Serrao; Z. L. Xu; B. Debnath; F. Christ; Z. Debyser; Y.Q. Long; N. Neamati; Bioorg. Med. Chem., 2013, 21, 5963–5972.

Y. Al-Soud; N. Al-Masoud; E. de Clerck; C. Pannecouque; Acta Pharm., 2007, 57, 379–393.

Y.L. Fan; X. H. Jin; Z.P. Huang; H.F. Yu; Z.G. Zeng; T. Gao; L.S. Feng; Eur. J. Med. Chem., 2018, 150, 347-365.

A. Campaniço; R. Moreira; F. Lopes; Eur. J. Med. Chem., 2018, 150, 525-545.

V. Antoci; D. Cucu; G. Zbancioc; C. Moldoveanu; V. Mangalagiu; D. Amariucai-Mantu; A. Aricu; I.I. Mangalagiu; Future Med. Chem., 2019, 11, in press.

C.N. Lungu; B.I. Bratanovici; M.M. Grigore; V. Antoci; I.I. Mangalagiu; Curr. Med. Chem., 2019, 26, in press.

D. Mantu; V. Antoci; C. Moldoveanu; G. Zbancioc; I.I. Mangalagiu; J. Enzyme Inhib. Med. Chem., 2016, 31(S2), 96–103.

A.M. Zbancioc; Ghe. Zbancioc; C. Tanase; A. Miron; C. Ursu; I.I. Mangalagiu; Lett. Drug. Des. Discov., 2010, 7, 644-649.

Y.X. Xu; H. Wang; X.K. Li; S.N. Dong; W.W. Liu; Q. Gong; T.D. Wang; Y. Tang; J. Zhu; J. Li; H.Y. Zhang; F. Mao; Eur. J. Med. Chem., 2018, 143, 33-47.

P. Molina; A. Tárraga; F. Otón; Org. Biomol. Chem., 2012, 10, 1711–1724.

M. Gaba; C. Mohan; Med. Chem. Res., 2016, 25, 173–210.

I. Zugravescu; M. Petrovanu; N-Ylid Chemistry, McGraw-Hill, London, New York, 1976, pp. 100-117.

I.I. Mangalagiu; I. Druta; M. Constantinescu; I. Humelnicu; M. Petrovanu; Tetrahedron, 1996, 52 (26), 8853-8862.

I.I. Mangalagiu; G. Mangalagiu; G. Drochioiu; C. Deleanu; M. Petrovanu; Tetrahedron, 2003, 59, 111-114.

M. Caprosu; Ghe. Zbancioc; C. Moldoveanu; I.I. Mangalagiu; Collect. Czech Chem. C., 2004, 69, 426-434.

G. Zbancioc; V. Bejan; M. Risca; C. Moldoveanu; I.I. Mangalagiu; Molecules, 2009, 14(1), 403-411.

R. Tucaliuc; V. Cotea; M. Niculaua; C. Tuchilus; D. Mantu; I.I. Mangalagiu; Eur. J. Med. Chem., 2013, 67, 367-372.

G. Zbancioc; I.I. Mangalagiu; C. Moldoveanu; Ultrason. Sonochem., 2015, 23, 376-383.

C.I. Ciobanu; V. Antoci; D. Mantu; I.I. Mangalagiu; Rev. Chim. Bucharest, 2015, 66(4), 497-498.

G. Zbancioc; C. Moldoveanu; I. Humelnicu; V. Vasilache; I.I. Mangalagiu; Rev. Chim. Bucharest, 2016, 67(8), 1516-1519.

C. Moldoveanu; G. Zbancioc; D. Mantu; D. Maftei; I.I. Mangalagiu; Plos One, 2016, 11 (5), e0156129 (1-9).

H. Ogura; K. Kikuchi; J. Org. Chem., 1972, 37, 2679-2682.

I. Zugravescu; J.M. Herdan; I. Druta; Rev. Roum. Chim., 1974, 19, 649-658.

I. Zugravescu; J.M. Herdan; I. Druta; Rev. Roum. Chim., 1974, 19, 659-664.

O. Meth-Cohn; Tetrahedron Lett., 1975, 413-416.

B. Wang; J. Hu; X. Zhang; Y. Hu; H. Hu; J. Heterocycl. Chem., 2000, 37, 1533-1537.

E. Georgescu; F. Georgescu; C. Roibu; P. C. Iuhas; C.Draghici; M. T. Caproiu; Rev. Roum. Chim., 2002, 47, 885-891.

K. Wu; Q.Y. Chen; Synthesis, 2003, 35-40.

X. Fang; Y.X. Wu; J. Deng; S.W. Wang, Tetrahedron, 2004, 60, 5487-5493.

A. Nicolescu; C. Deleanu; E. Georgescu; F. Georgescu; A.M. Iurascu; S. Shova; P. Filip; Tetrahedron Lett., 2013, 54, 1486-1488.

E. Georgescu; A. Nicolescu; F. Georgescu; F. Teodorescu; D. Marinescu; A.M. Iurascu-Macsim; C. Deleanu; Beilstein J. Org. Chem., 2014, 10, 2377-2387.

E. Georgescu; A. Nicolescu; F. Georgescu; F. Teodorescu; S. Shova; A.M. Macsim; C. Deleanu; Synthesis, 2015, 47, 1643-1655.

E. Georgescu; A. Nicolescu; F. Georgescu; S. Shova; B.C. Simionescu; C. Deleanu; Rev. Roum. Chim., 2016, 61(4-5), 283-290.

E. Georgescu; A. Nicolescu; F. Georgescu; F. Teodorescu; S. Shova; A.T. Marinoiu; A.F. Dumitrascu; C. Deleanu; Tetrahedron, 2016, 72, 2507-2520.

STUDIA UBB CHEMIA, Volume 64 (LXIV), No. 3, September 2019

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Published

2019-09-30

How to Cite

CUCU, D. ., MANGALAGIU, V. ., AMARIUCAI-MANTU, D. ., ANTOCI, V. ., & MANGALAGIU, I. I. . (2019). IMIDAZOLIUM YLIDES: CYCLOADDITION versus HYDROLISIS. Studia Universitatis Babeș-Bolyai Chemia, 64(3), 59–66. https://doi.org/10.24193/subbchem.2019.3.05

Issue

Volume 64, No. 3, 2019

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