Functionalization of dipyrromethanes via hetero-Diels–Alder reaction with azo- and nitrosoalkenes

Pereira, Nelson A. M.; Lemos, A.; Serra, Arménio C.; Melo, Teresa M. V. D. Pinho e

http://hdl.handle.net/10400.1/5687

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Authors

Pereira, Nelson A. M.

Lemos, A.

Serra, Arménio C.

Melo, Teresa M. V. D. Pinho e

Abstract(s)

5,50-Diethyl- and 5-phenyldipyrromethanes participate in cycloadditions with azo- and nitrosoalkenes giving dipyrromethanes with side chains containing open chain oximes and hydrazones. By controlling reaction stoichiometry it is possible to get mono or 1,9-disubstituted derivatives. The reported methodology gave access to a range of dipyrromethanes with good structural features for various applications. It was demonstrated that reduction of dipyrromethanes containing a-oximino ester groups opens the way to new a-amino esters.

Keywords

Dipyrromethanes Azoalkenes Nitrosoalkenes Hetero-Diels–Alder reaction

URI

http://hdl.handle.net/10400.1/5687

Citation

Pereira, Nelson A.M.; Lemos, Américo; Serra, Arménio C.; Pinho e Melo, Teresa M.V.D.Functionalization of dipyrromethanes via hetero-Diels–Alder reaction with azo- and nitrosoalkenes, Tetrahedron Letters, 54, 12, 1553-1557, 2013.