Diels-Alder reactions of 3-(1H-tetrazol-5-yl)-nitrosoalkenes: synthesis of functionalized 5-(substituted)-1H-tetrazoles

被引：32
|
作者：
Lopes, Susana M. M. [2 ]
Palacios, Francisco [3 ]
Lemos, Americo [1 ]
Pinho e Melo, Teresa M. V. D. [2 ]
机构：
[1] Univ Algarve, FCT, CIQA, P-8005139 Faro, Portugal
[2] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal
[3] Univ Basque Country, Fac Pharm, Dept Organ Chem 1, Vitoria 01080, Spain
来源：
TETRAHEDRON | 2011年 / 67卷 / 46期
关键词：
PHOSPHONYL-NITROSO ALKENES; N-BENZYLAMINO DERIVATIVES; ELECTRON-RICH ALKENES; CYCLOADDITION REACTIONS; ETHYL; 2-NITROSOACRYLATE; EFFICIENT SYNTHESIS; RING CONTRACTION; BIOISOSTERES; TETRAZOLES; 1,2-OXAZINES;
D O I：
10.1016/j.tet.2011.09.051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general route to 12-oxazines and open chain oximes bearing a 1H-tetrazolyl substituent via Diels-Alder reaction of 3-(tetrazol-5-yl)-nitrosoalkenes is reported. It was also demonstrated that reduction of these adducts followed by deprotection of the tetrazolyl group give 5-(1-aminoalkyl)-1H-tetrazoles, alpha-amino acid analogues. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8902 / 8909
页数：8
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