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Synthesis of naphthothiophene derivatives through polar Diels-Alder reactions employing 5-nitrobenzothiophene as electrophile. Microwave irradiation vs classical thermal conditions
Published:
30 October 2015
by MDPI
in The 19th International Electronic Conference on Synthetic Organic Chemistry
session Microwave Assisted Synthesis
Abstract:
Herein we report a simple, economical and efficient one-step procedure to synthesize the naphtho[2,1-b]thiophene ring system in good to excellent yield through the polar Diels-Alder reactions of 5-nitro-3-acetylbenzothiophene and dienes of different nucleophilicity. In thermal conditions the reactions were developed in molecular solvents; moreover the reaction system was exposed to microwave irradiation as a complement of reaction conditions.
Keywords: Nitrobenzothiophene, electrophile, Diels-Alder
Comments on this paper
Murali Venkata Basavanag Unnamatla
4 November 2015
elimination of nitro group in the reaction
hello madam
congratulation to your work but i have small question, while observing the reaction i have seen that there was elimination of Nitro group during the reaction, can you please explain how it is possible .
congratulation to your work but i have small question, while observing the reaction i have seen that there was elimination of Nitro group during the reaction, can you please explain how it is possible .
Claudia Della Rosa
4 November 2015
Hello, It has been demonstrated that in contrast to the acylated aromatic heterocycles, nitro aromatic heterocycles, such as nitrofurans, nitropyrroles, nitrothiophenes, nitro selenophenes, nitrobenzofurans, nitroindoles and nitrobenzothiophenes react efficiently with the different dienes in polar Diels-Alder reactions, with the nitro group inducing side selectivity. This substituent is easily extrused under thermal conditions.
All addition products showed extrusion of the nitro group as nitrous acid.
References
1- Domingo, L. R.; Aurell, M. J.; Kneeteman, M. N.; Mancini, P. M. E. J. Mol. Struc. (Theochem), 2008, 853,68-76.
2- C. Della Rosa, C. Ormachea, M.N. Kneeteman, C. Adam, P.M.E. Mancini, Tetrahedron Letters, 2011, 52, 6754-6757
3- Della Rosa, C. D.; Sanchez, J. P.; Kneeteman, M. N.; Mancini, P. M. E. Tetrahedron Lett. 2011, 52, 2316-2319.
4- Della Rosa, C. D.; Ormachea, C. M.; Sonzogni, A. S.; Kneeteman, M. N.; Domingo, L. R.; Mancini, P. M. E. Lett. in Org. Chem. 2012, 9, 691-695.
5- C. D. Della Rosa, P.M.E. Mancini, M.N. Kneeteman, A.F. López Baena, M. Suligoy, L.R. Domingo. Journal of Molecular Structure, 2015, 1079, 47-53.
All addition products showed extrusion of the nitro group as nitrous acid.
References
1- Domingo, L. R.; Aurell, M. J.; Kneeteman, M. N.; Mancini, P. M. E. J. Mol. Struc. (Theochem), 2008, 853,68-76.
2- C. Della Rosa, C. Ormachea, M.N. Kneeteman, C. Adam, P.M.E. Mancini, Tetrahedron Letters, 2011, 52, 6754-6757
3- Della Rosa, C. D.; Sanchez, J. P.; Kneeteman, M. N.; Mancini, P. M. E. Tetrahedron Lett. 2011, 52, 2316-2319.
4- Della Rosa, C. D.; Ormachea, C. M.; Sonzogni, A. S.; Kneeteman, M. N.; Domingo, L. R.; Mancini, P. M. E. Lett. in Org. Chem. 2012, 9, 691-695.
5- C. D. Della Rosa, P.M.E. Mancini, M.N. Kneeteman, A.F. López Baena, M. Suligoy, L.R. Domingo. Journal of Molecular Structure, 2015, 1079, 47-53.
