[4+2] Cycloadditions of 3-Tetrazolyl-1,2-diaza-1,3-butadienes: synthesis of 3-Tetrazolyl-1,4,5,6-tetrahydropyridazines

Lopes, Susana M. M.; Brigas, Amadeu; Palacios, Francisco; Lemos, A.; Melo, Teresa M. V. D. Pinho e

http://hdl.handle.net/10400.1/1045

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Authors

Melo, Teresa M. V. D. Pinho e

Abstract(s)

The synthesis of new 3-tetrazolyl-1,4,5,6-tetrahydropyridazines by Diels–Alder reactions of ethyl 3-(tetrazol-5-yl)-1,2- diaza-1,3-butadiene-1-carboxylates is reported. These 1,2- diaza-1,3-dienes reacted with electron-rich heterocycles, nucleophilic olefins and cumulenes, as well as with electrondeficient dienophiles, to give the target compounds regioselectively. Computational studies corroborated the rationalization of the observed reactivity and selectivity.

Keywords

Heterocycles Aza-Diels-alder Azoalkene Pyridazine

URI

http://hdl.handle.net/10400.1/1045

Citation

Lopes, Susana M. M.; Brigas, Amadeu F.; Palacios, Francisco; Lemos, A.; Melo, Teresa M. V. D. Pinho e. [4+2] Cycloadditions of 3-Tetrazolyl-1,2-diaza-1,3-butadienes: synthesis of 3-Tetrazolyl-1,4,5,6-tetrahydropyridazines. European Journal of Organic Chemistry, 2012, 11, 2152-2160, 2012.