1990 Fiscal Year Final Research Report Summary
Selective Synthesis of Indole Derivative by Molecular Complex Formation
| Project/Area Number |
01850195
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| Research Category |
Grant-in-Aid for Developmental Scientific Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tokyo University of Science |
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Principal Investigator |
HIRAI Hidefumi Science University of Tokyo, Department of Industrial Chemistry, Professor, 工学部, 教授 (90010751)
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| Co-Investigator(Kenkyū-buntansha) |
AOSHIMA Jyun Asahi Chemical Industry, Co., Ltd. Research Laboratory, General Manager, 所長
YOSHINO Norio Science University of Tokyo, Department of Industrial Chemistry, Lecturer, 工学部, 講師 (50084380)
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| Project Period (FY) |
1991 – 1992
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| Keywords | Cyclodextrin / Indole / Indole-3-aldehyde / 3-Chloroquinoline / Dichlorocarbene / Chloroform / Continuous addition method |
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| Research Abstract |
Indole was reacted with chloroform in alkaline solution at 60^ﾟC, for 10 hr, yielding indole-3-aldehyde and 3-chloroquinoline. The addition of beta-cyclodextrin increased the yield of indole-3-aldehyde from 8.7 mol% to 16.2 mol%. Continuous additions both of chloroform and of 4N NaOH aqueous solution for 10 hr, in the absence of beta-cyclodextrin, gave indole-3-aldehyde in 24.0 mol% and 3-chloroquinoline in 1.3 mol% yield, and those in the presence of beta-cyclodextrin gave indole-3-aldehyde in 45.8 mol% and 3-chloroquinoline in 10.1 mol%. The effects of alkaline concentration, the addition method of chloroform, the concentration of beta-cyclodextrin, and the reaction temperature on the yield and selectivity of indole-3-aldehyde were investigated. The role of the cyclodextrin was attributed to the molecular complex formation of cyclodextrin both with indole and with chloroform.
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