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A hetero-Diels–Alder approach to functionalized 1H-tetrazoles: synthesis of tetrazolyl-1,2-oxazines, -oximes and 5-(1-aminoalkyl)-1H-tetrazoles
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Orientador(es)
Resumo(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.
Descrição
Palavras-chave
5-(1-Aminoalkyl)-1H-tetrazoles Nitrosovinyltetrazole Cycloaddition Oxime Oxazine
Contexto Educativo
Citação
Lopes, Susana M.M.; Lemos, A.; Melo, Teresa M.V.D. Pinho 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, 6756-6759, 2010.