Electrocyclic Ring-Opening of 1,2,4-Oxadiazole[4,5-a]piridinium Chloride: a New Route to 1,2,4-Oxadiazole Dienamino Compounds

被引:3
作者
Carella, Stefano [1 ]
Memeo, Misal Giuseppe [1 ]
Quadrelli, Paolo [1 ]
机构
[1] Univ Pavia, Dept Chem, Viale Taramelli 12, I-27100 Pavia, Italy
关键词
nitrile oxides; 1; 3-dipolar cycloadditions; Zincke salts; oxadiazoles; dienamino derivatives; NITRILE OXIDES; NUCLEOPHILES; DIMERIZATION; BEHAVIOR; NMR;
D O I
10.1002/open.201900230
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,2,4-Oxadiazole[4,5-a]piridinium chloride adds nucleophiles to undergo electrocyclic ring opening affording 1,2,4-oxadiazole dienamino derivatives. These pyridinium salts represent a special class of Zincke salts that are prone to rearrange when treated with primary amines or in the presence of bicarbonate to give the pyridones. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole dienamine derivatives. The mechanism is also discussed in the light of NMR experiments and theoretical calculations.
引用
收藏
页码:1209 / 1221
页数:13
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