| Novel Preparation of Methoxy Carbamates of 1-Protected Indole- 3-methylamines as Precursor of Indole-3-methylamine |
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| 作者姓名： | SONG Hao
XIN Jun-Guo
WANG Yin
CHEN Wei
YANG Jun
QIN Yong |
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| 作者单位： | SONG,Hao（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041）
XIN,Jun-Guo（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041）
WANG,Yin（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041）
CHEN,Wei（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041）
YANG,Jun（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041）
QIN,Yong（Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041） |
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| 基金项目： | 国家自然科学基金，Ministry of Education (EYTP) Foundation |
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| 摘 要： | Indole-3-methylamine (1) has been well demonstrated to be a very useful intermediate as a pharmaceutical building block and starting material for syntheses of phytoalexins.1] The instability of indole-3-methylamine (1) has undoubtedly restricted its application in synthetic chemistry. Hofmann rearrangement that directly converts carboxamides to alky carbamates in the presence of alcohol required unexceptionally a strong base,2] which devaluated the possible usefulness of Hofmann rearrangement in preparation of base sensitive amines, especially for the preparation of unstable indole-3-methylamine (1). Herein we would like to report a convenient method for the preparation of alkyl carbamates of 1-protected indole-3-methylamines (4) via the diacetoxyiodobenzene (DIB) promoted Hofmann rearrangement under neutral condition.
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Novel Preparation of Methoxy Carbamates of 1-Protected Indole- 3-methylamines as Precursor of Indole-3-methylamine |
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| SONG,Hao,XIN,Jun-Guo,WANG,Yin,CHEN Wei,YANG,Jun,QIN,Yong.Novel Preparation of Methoxy Carbamates of 1-Protected Indole- 3-methylamines as Precursor of Indole-3-methylamine[J].Chinese Journal of Organic Chemistry,2004,24(Z1):249. |
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| Authors: | SONG Hao XIN Jun-Guo WANG Yin CHEN Wei YANG Jun QIN Yong |
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| Abstract: | Indole-3-methylamine (1) has been well demonstrated to be a very useful intermediate as a pharmaceutical building block and starting material for syntheses of phytoalexins.1] The instability of indole-3-methylamine (1) has undoubtedly restricted its application in synthetic chemistry. Hofmann rearrangement that directly converts carboxamides to alky carbamates in the presence of alcohol required unexceptionally a strong base,2] which devaluated the possible usefulness of Hofmann rearrangement in preparation of base sensitive amines, especially for the preparation of unstable indole-3-methylamine (1). Herein we would like to report a convenient method for the preparation of alkyl carbamates of 1-protected indole-3-methylamines (4) via the diacetoxyiodobenzene (DIB) promoted Hofmann rearrangement under neutral condition. |
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