Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters

Mirosław Gucma, W. Marek Golebiewski, Krzysztof Zelechowski, Maria Krawczyk

Abstract


[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.

Keywords


dipolar cycloaddition; abietates; site selectivity; NMR spectroscopy

References


Janocha, D. Schmitz, R. Bernhardt, Adv. Biochem. Eng. /Biotech. 148 (2015) 215 (https://doi.org/10.1007/10_2014_296)

M. A. González, D. Pérez-Guaita, J. Correa-Royero, B. Zapata, L. Agudelo, A. Mesa-Arango, L. Betancur-Galvis, Eur. J. Med. Chem. 45 (2010) 811 (https://doi.org/10.1016/j.ejmech.2009.10.010)

R. A. S. Schweizer, A. G. Atanasov, B. M. Frey, A. Odermatt, Mol. Cell Endocrinol. 212 (2003) 41 (https://doi.org/10.1016/j.mce.2003.09.027)

A. X. Lupea, F. Radu, I. Gergen, Rev. Chim. Bucharest 54 (2003) 923

M. A. González, J. Correa-Royero, L. Agudelo, A. Mesa, L. Betancur-Galvi, Eur. J. Med. Chem. 44 (2009) 2468 (https://doi.org/10.1016/j.ejmech.2009.01.014)

G. C. Justino, C. F. Correia, L. Mira, R. M. Borges dos Santos, J. A. Martinho Simões, A. M. Silva, C. Santos, B. Gigante, J. Agric. Food Chem. 54 (2006) 342 (https://doi.org/10.1021/jf052062k)

K. Bast, M. Christl, R. Huisgen, W. Mack, R. Sustman, Chem. Ber. 106 (1973) 3258 (https://doi.org/10.1002/cber.19731061015)

S. Ghorai, R. Mukhopadhyay, A. P. Kundu, A. Bhattacharjya, Tetrahedron 61 (2005) 2999 (https://doi.org/10.1016/j.tet.2005.01.1)

P. J. Zimmermann, I. Blanarikova, A. Juger, Angew. Chem. Int. Ed. 39 (2000) 910 (https://doi.org/0570-0833/00/3905-0912)

T. Mukayama, T. Hoshino, J. Am. Chem. Soc. 82 (1960) 5339 (https://doi.org/10.1021/ja01505a017)

T. Shimizu, T. Hayashi, H. Shibafuchi, K. Teramura, Bull. Chem. Soc. Jpn. 59 (1986) 2827 (https://doi.org/10.1246/bcsj.59.2827)

P. Caramella, P. Grunanger, in 1,3-DipolarCycloaddition Chemistry, A. Padwa (ed), Wiley, New York, 1984, p 177

L. Fisera, V. Ondrus, H. J. Timpe, Collect. Czech. Chem. Commun. 55 (1990) 512 (https://doi.org/10.1135/cccc19900512)

M. Gucma, W. M. Gołębiewski, M. Krawczyk, J. Braz. Chem. Soc. 24 (2013) 805 (http://dx.doi.org/10.5935/0103-5053.20130106)

M. Gucma, W. M. Gołębiewski, A. K. Michalczyk, Monatsh. Chem. 147 (2016) 1809 (https://doi.org/10.1007/s00706-016-1797-4)

S. Mitra, K. P. Ganewatta, S. Miller, S. Parker, P. Mehrpouya-Bahrami, Y. P. Chen,; Y. Yan, M. Nagarkatti, P. Nagarkatti, A. W. Decho, C. Tang, Biomacromolecules 16 (2015) 3336 (https://doi.org/10.1021/acs.biomac.5b01005)

K. C. Liu, B. R. Shelton, R. K. Howe, J. Org. Chem. 45 (1980), 3916 (https://doi.org/10.1021/jo01307a039)

B. Zhou, X. Li, H. Feng, Y. Li, Tetrahedron 66 (2010) 5396 (https://doi.org/10.1016/j.tet.2010.05.035)

D. F. Taber, J. F. Berry, T. J. Martin, J. Org. Chem. 73 (2008) 9334 (https://doi.org/10.1021/jo801781v)

B. Bhattarai, J.-H. Tay, P. Nagorny, Chem. Commun. 51 (2015) 5398 (http://doi.org/10.1039/C4CC08604J)

K. H. Houk, J. Sims, C. R. Watts, L. J. Jenkins, J. Am. Chem. Soc. 95 (1973) 7301 (https://doi.org/ 10.1021/ja00803a018)

H.-J. Schneider, U. Buchheit, N. Becker, G. Schmidt, U. Siehl, J. Am. Chem. Soc. 107 (1985) 7027 (https://doi.org/10.1021/ja00310a046)




DOI: https://doi.org/10.2298/JSC180517018G

Copyright (c) 2019 J. Serb. Chem. Soc.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

IMPACT FACTOR 0.828 (140 of 172 journals)
5 Year Impact Factor 0.917 (140 of 172 journals)