Alkylation and arylation of pyrazoles under solvent-free conditions:: Conventional heating versus microwave irradiation

被引:31
作者
Almena, I [1 ]
Díez-Barra, E
de la Hoz, A
Ruiz, J
Sánchez-Migallón, A
Elguero, J
机构
[1] Univ Castilla La Mancha, Fac Quim, Dept Quim Organ, E-13071 Ciudad Real, Spain
[2] CSIC, Inst Quim Med, E-28006 Madrid, Spain
关键词
D O I
10.1002/jhet.5570350604
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of sodium hydrogen carbonate under solvent-free conditions and microwave irradiation is by far the best method for N-alkylating pyrazoles. The yields are good and the method is devoid of side reactions (quaternization, isomerization, hydrogen halide elimination). Solvent-free conditions are the only ones that allow us to prepare 1-substituted pyrazoles from secondary halides. The procedure using quaternary salts in one-pot provides an interesting alternative for the preparation of 1-heteroarylpyrazoles.
引用
收藏
页码:1263 / 1268
页数:6
相关论文
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