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

被引：27

作者：

Lopes, Susana M. M. ^{[2
]}

Lemos, Americo ^{[1
]}

Pinho e Melo, Teresa M. V. D. ^{[2
]}

机构：

[1] Univ Algarve, CIQA, FCT, P-8005139 Faro, Portugal

[2] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 51期

关键词：

5-(1-Aminoalkyl)-1H-tetrazoles; Nitrosovinyltetrazole; Cycloaddition; Oxime; Oxazine; ELECTRON-RICH ALKENES; TETRAZOLE ANALOGS; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; BIOISOSTERES; INHIBITORS; PYRROLES; DERIVATIVES; CHEMISTRY; EFFICIENT;

D O I：

10.1016/j.tetlet.2010.10.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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,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 alpha-amino acids. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6756 / 6759

页数：4

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