反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[C:8]3[CH2:12][C:11]([C:6]=2[CH:5]=1)=[CH:10][CH:9]=3)([O-])=O>[Ni].[Pd].CO>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[CH:8]3[CH2:12][CH:11]([C:6]=2[CH:5]=1)[CH2:10][CH2:9]3参加物
実験手順
In the synthesis shown in Scheme 1, a 3-nitrobenzene, generated from a 6-nitro-anthranilic acid (A), is reacted with a cyclic 1,4-diene (B), such as 5-isopropyl-cyclopentadiene, to form a 5-nitro-benzonorbornadiene (C) in a Diels-Alder reaction. Under standard catalytic reduction conditions (for example, using Raney nickel or palladium on carbon in a solvent such as methanol), both the 5-nitro group and the 2,3-double bond of the 5-nitro-benzonorbornadiene (C) are reduced to form the 5-amino-benzonorbornene (D). Reaction of the 5-amino-benzonorbornene (D) with a heterocyclyl-carboxylic acid or heterocyclyl-carboxylic acid derivative (E), where Q may be hydroxyl, fluoro, chloro or bromo, in a solvent such as dichloromethane gives a fungicidal heterocyclyl-carboxylic acid benzonorbornen-5-yl-amide (F). An example of (D) is 5-amino-9-isopropyl-benzonorbornene, which is a precursor of an amide of, for example, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid.
後処理
- customin a Diels-Alder reaction
出典と根拠
- ORDレコード
- ord-c2cd276fa13040e19f60541e92577d6f
- 出典データセット
- uspto-grants-2010_08
- 特許番号
- US07781615B2
関連ノート
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