Susana M. M. Lopes, Américo Lemos, T. P. Melo
Dec 22, 2010
Citations
0
Influential Citations
28
Citations
Journal
Tetrahedron Letters
Abstract
Abstract This work describes the first and unprecedented examples of inverse electron demand Diels–Alder reactions of 5-(1-nitrosovinyl)-1-phenyl-1 H -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)-1 H -tetrazoles, paving the way for a new entry into this important class of compounds, bioisosteres of α-amino acids.