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

✍ Scribed by Susana M.M. Lopes; Américo Lemos; Teresa M.V.D. Pinho e Melo

• Book ID: 104098495
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 1023 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.10.095

✦ Synopsis

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.