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| 1.
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Yamada, Koji ; Tomioka, Saori ; Tanizawa, Noriko ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Hydroxy-6- and -5-nitroindole-3-carbaldehydes are prepared for the first time
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from 1-methoxy-6- and -5-nitroindole-3-carbaldehydes, respectively, based on the discovery of novel methyl ether cleavage reaction. Utilizing them as common synthetic intermediates, syntheses of several daikon-phytoalexin analogs are achieved.
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| 2.
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Yamada, Koji ; Kanbayashi, Yukiko ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Syntheses of wasabi phytoalexin analogs, such as 6-bromo-5-iodo, 2-bromo-5-iodo
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, 6-nitro, 5-chloroacetyl, and 6-chloroacetyl congeners, are reported. An interesting effect of the 1-methoxy group on the regioselectivity of electrophilic substitution reactions on indole nucleus is observed.
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| 3.
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Yamada, Koji ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />Nucleophiles react with 1-methoxy-3-(2-nitrovinyl)indole (3) at the 2-position regioselectiv
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ely in a dipolar aprotic solvent (DMF or HMPA), while in THF they undergo Michael addition to the β-carbon of nitrovinyl side chain. Depending on bases employed, the resultant Michael addition products (6d, 10, and 11) are found to undergo interesting cyclizations to give novel 3-substituted 1-methoxyindoles (7, 9, and 12).
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| 4.
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Somei, Masanori ; Noguchi, Koichi ; Yamagami, Ryutaro ; Kawada, Yumiko ; Yamada, Koji ; Yamada, Fumio
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金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Novel 9-hydroxy-β-carboline derivatives were produced for the first time. A nov
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el rearrangement reaction of 1, 2, 3, 4-tetrahydro-9-hydroxy-β-carbolines was discovered to give 3, 3-disubstituted oxindoles, which was successfully applied to the total synthesis of (±)-coerulescine.
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| 5.
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Somei, Masanori ; Morikawa, Harunobu ; Yamada, Koji ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Hydroxytryptamines (6a-f) having (E)-3-phenyl-, (E)-3-(4-hydroxyphenyl)-, (E)
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-3-(4-hydroxy-3-methoxyphenyl)propenoyl, octanoyl, hexadecanoyl, and docosanoyl group as a Nb-substituent are prepared for the first time. Preparations of serotonins (2a-c, e) from the corresponding 1-hydroxytryptamines (6a-c, e) are also reported. A novel homologation on the 3-substituent of 1-hydroxytryptamines is discovered upon treatment with diazomethane in chloroform or dichloromethane.
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| 6.
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile substrate fo
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r the nucleophilic substitution reactions providing 2,3,6-trisubstituted indole derivatives. Preparation of a novel pyrimido[1,2-a]indole derivative is also reported.
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| 7.
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Yamada, Fumio ; Hayashi, Toshikatsu ; Yamada, Koji ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A lithium hydroxide promoted glucosidation of 1-hydroxyindoles with 2, 3, 4, 6-
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tetra-0-acetyl-α-D-glucopyranosyl bromide is newly developed. Applying this method, the first and simple syntheses of novel indol-1-yl glucosides were achieved.
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| 8.
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Hayashi, Toshikatsu ; Peng, Wu ; Nakai, Yu-ya ; Yamada, Koji ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nit
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rogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.
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| 9.
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Yamada, Koji ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nit
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rogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.<br />An easy approach to 7-substituted 4,5-dihydro-7H-pyrano[3,4-c]-isoxazole derivatives (3a-b and 6a-d) is described by the reaction of 2-aryl substituted 1-nitro-3-oxa-6-heptynes (2, 5a and 5b) with n-BuLi, followed by treatment with acetic anhydride.
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| 10.
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Yamada, Koji ; Izumi, Tomoyuki ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Methoxy-3-(2-nitrovinyl)indole (1a) functions as an electrophile and reacts w
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ith various nucleophiles. In THF, nucleophiles undergo conjugate addition to the β-carbon of the nitroviyyl side chain of 1a, regioselectively. The resultant Michael addition products (4d and 8) cyclize to novel 3-substituted 1-methoxyindoles (5 and 7) depending on reaction conditions and a plausible mechanism is discussed. In dipolar aprotic solvent (DMF), nucleophiles react with 1a at the 2-position predominantly with concomitant liberation of the 1-methoxy group giving 2-substituted indoles. © 2005 The Japan Institute of Heterocyclic Chemistry.
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