Reaction of N-methyl-5-tributylstannyl-4-fluoro-1H-pyrazole and its application to N-methyl-chromeno[2,3-d]pyrazol-9-one synthesis

被引：13

作者：

Hanamoto, Takeshi ^{[1
]}

Hashimoto, Eri ^{[1
]}

Miura, Masayuki ^{[1
]}

Furuno, Hiroshi ^{[2
]}

Inanaga, Junji ^{[2
]}

机构：

[1] Saga Univ, Dept Chem & Appl Chem, Saga 8408502, Japan

[2] Kyushu Univ, IMCE, Higashi Ku, Fukuoka 8128581, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 12期

关键词：

D O I：

10.1021/jo800431t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Methylation by sequential treatment of 5-tributylstannyl-4-fluoro-1H-pyrazole 1 with LDA and iodomethane regioselectively afforded the compound 2a in high yield. The addition reaction of 5-lithiated-4-fluoro-1H-pyrazole generated from 2a with a wide range of electrophiles allowed a facile introduction of different substituents at position 5 in good yields. The adduct 3d was efficiently converted to N-methyl-chromeno[2,3-d]pyrazol-9-one 9 in 3 steps.

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页码：4736 / 4739

页数：4

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