AZIDE RING-OPENING RING-CLOSURE REACTIONS AND TELE-SUBSTITUTIONS IN VICINAL AZIDOPYRAZOLECARBOXALDEHYDES, PYRROLECARBOXALDEHYDES AND INDOLECARBOXALDEHYDES

被引:40
作者
BECHER, J
JORGENSEN, PL
PLUTA, K
KRAKE, NJ
FALTHANSEN, B
机构
[1] Department of Chemistry, Odense University, Odense M
关键词
D O I
10.1021/jo00033a039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
引用
收藏
页码:2127 / 2134
页数:8
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