The use of isoprene as a dienophile in stereo- regioselective synthesis of new isoindolo[2,1-a]quinolin-11(5H)-ones via PMA-catalyzed three component Povarov reaction

The use of isoprene as a dienophile in stereo- regioselective synthesis of new isoindolo[2,1-a]quinolin-11(5H)-ones via PMA-catalyzed three component Povarov reaction

Merchán Arenas, D. R.; Kouznetsov, V. V.

Abstract:

The research about of the isoprene system (2- methyl-1,3-butadiene) have effects in some relevant scientific areas as environmental, phytochemical, polymers, etc. However, their more interesting synthetic applications consist in the construction of new molecular models with the isoprenyl moiety, because many natural and synthetic isoprene-based products are widely used in the pharmaceutical, cosmetic, and alimentary industry due to its biochemical features. This molecule represents an important precursor in the Diels-Alder reaction, generally used as an active diene in the synthesis of carbocyclic adducts and some rare heterocyclic compounds. In our research we used this molecule as an electron-rich dienophile in the little explored Povarov reaction, catalyzed by phosphomolybdic acid (PMA) in MeCN to obtain the new 5-methyl-5- vinyl-isoindolo[2,1-a]quinolin-11(5H)-ones.

The research about of the isoprene system (2- methyl-1,3-butadiene) have effects in some relevant scientific areas as environmental, phytochemical, polymers, etc. However, their more interesting synthetic applications consist in the construction of new molecular models with the isoprenyl moiety, because many natural and synthetic isoprene-based products are widely used in the pharmaceutical, cosmetic, and alimentary industry due to its biochemical features. This molecule represents an important precursor in the Diels-Alder reaction, generally used as an active diene in the synthesis of carbocyclic adducts and some rare heterocyclic compounds. In our research we used this molecule as an electron-rich dienophile in the little explored Povarov reaction, catalyzed by phosphomolybdic acid (PMA) in MeCN to obtain the new 5-methyl-5- vinyl-isoindolo[2,1-a]quinolin-11(5H)-ones.

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DOI: 10.5151/chempro-14bmos-R0378-1

Referências bibliográficas

• [1] 1Pacifico, F.; Harrison, S. P.; Jones, C. D. and Sitch, S. Atmospheric Environment, 2009, 43, 6121-6135.
• [2] 2Velikova, V. B. J. Plant Interactions, 2008, 3, 1-15.
• [3] 3Garate, H.; Fascio, M. L.; Mondragon, I.; D’Accorso, N. B.; Goyanes, S. Polymer, 2011, 52, 2214-2220.
• [4] 4Shing, T. K. M.; Lo, H. Y. and Mak, T. C. W. Tetrahedron, 1999, 55, 4643-4648.
• [5] 5Kobayashi, S.; Ishitani, H. and Nagayama, S. Synthesis, 1995, 9, 1195-1202.

Como citar:

Merchán Arenas, D. R.; Kouznetsov, V. V.; "The use of isoprene as a dienophile in stereo- regioselective synthesis of new isoindolo[2,1-a]quinolin-11(5H)-ones via PMA-catalyzed three component Povarov reaction", p-378-378. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0378-1