A hetero-Diels-Alder approach to functionalized 1H-tetrazoles: synthesis of tetrazolyl-1,2-oxazines, -oximes and 5-(1-aminoalkyl)-1H-tetrazoles

Lopes, Susana M. M.; Lemos, A.; Melo, Teresa M. V. D. Pinho e

http://hdl.handle.net/10400.1/5685

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Authors

Lopes, Susana M. M.

Lemos, A.

Melo, Teresa M. V. D. Pinho e

Abstract(s)

This work describes the first and unprecedented examples of inverse electron demand Diels–Alder reactions of 5-(1-nitrosovinyl)-1-phenyl-1H-tetrazole, generated in situ from the corresponding bromooxime, with electron rich alkenes and heterocycles, providing in good overall yields tetrazolyl-1,2-oxazines and -oximes. Upon subsequent reduction these allowed the access to 5-(1-aminoalkyl)-1H-tetrazoles, paving the way for a new entry into this important class of compounds, bioisosteres of a-amino acids.

Keywords

5-(1-Aminoalkyl)-1H-tetrazoles Nitrosovinyltetrazole Cycloaddition Oxime Oxazine

URI

http://hdl.handle.net/10400.1/5685

Citation

Lopes, S.M.M.; Lemos, A.; Melo, T.M.V.D.P.E.A hetero-Diels-Alder approach to functionalized 1H-tetrazoles: Synthesis of tetrazolyl-1,2-oxazines, -oximes and 5-(1-aminoalkyl)-1H-tetrazoles, Tetrahedron Letters, 51, 51, 6756-67, 2010.