Solvent effect on the reaction of 1-methoxy-3-(2-nitrovinyl)indole with nucleophiles

Solvent effect on the reaction of 1-methoxy-3-(2-nitrovinyl)indole with nucleophiles

フォーマット:

論文

責任表示:

Yamada, Koji ; Izumi, Tomoyuki ; Yamada, Fumio ; Somei, Masanori

言語:

英語

出版情報:

日本複素環化学研究所, 2005-12-31

著者名:

掲載情報:

Heterocycles

巻:

66

通号:

1

開始ページ:

583

終了ページ:

594

バージョン:

publisher

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 with various nucleophiles. In THF, nucleophiles undergo conjugate addition to the β-carbon of the nitrov … iyyl 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. 続きを見る

URL:

http://hdl.handle.net/2297/4383

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受理日:	2005-12-31

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1 論文 Reactions of 1-methoxy-3-(2-nitrovinyl)indole with nucleophiles: An interesting solvent effect and a novel preparation of 3-substituted 1-methoxyindoles Yamada, Koji, Yamada, Fumio, Somei, Masanori 日本複素環化学研究所	7 論文 The Chemistry of Indoles. CVII. A Novel Synthesis of 3, 4, 5, 6-Tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles and a New Finding on Pictet-Spengler Reaction Somei, Masanori, Teranishi, Sakiko, Yamada, Koji, Yamada, Fumio Pharmaceutical Society of Japan = 日本薬学会
2 論文 Nucleophilic substitution reaction in indole chemistry: 1-methoxy-6-nitroindole-3-carbaldehyde as a versatile building block for 2,3,6-trisubstituted indoles Yamada, Koji, Yamada, Fumio, Shiraishi, Takei, Tomioka, Saori, Somei, Masanori The Japan Institute of Heterocyclic Chemistry / Elsevier	8 論文 Nucleophilic substitution reaction of 1-methoxy-6-nitro-indole Yamada, Koji, Kawasaki, Toshiya, Fujita, Tomomi, Somei, Masanori 日本複素環化学研究所
3 論文 Nucleophilic Substitution Reaction in Indole Chemistry: 1-Methoxy-6-nitroindole-3-carbaldehyde as a Versatile Building Block for 2,3,6-Trisubstituted Indoles Yamada, Koji, Yamada, Fumio, Shiraishi, Takei, Tomioka, Saori, Somei, Masanori Japan Institute of Heterocyclic Chemistry = 日本複素環化学研究所	9 論文 Synthesis of 3a-(indol-3-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole core of leptosins D-F based on nucleophilic substitution reaction on indole nucleus Yamada, Fumio, Goto, Aya, Somei, Masanori 日本複素環化学研究所
4 論文 A novel synthetic method of pyrrolo[2,3-b]indoles and its application to the synthesis of (±)-debromoflustramine B1 Somei, Masanori, Yamada, Fumio, Izumi, Tomoyuki, Nakajou, Masahiro 日本複素環化学研究所	10 論文 Nucleophilic substitution reaction in indole chemistry: A synthesis of novel 7β-substituted yohimbine and 4aα-substituted 1,2,3,4-tetrahydro-β-carboline … Yoshino, Katsumasa, Yamada, Fumio, Somei, Masanori Japan Institute of Heterocyclic Chemistry = 日本複素環化学研究所
5 論文 Nucleophilic substitution reactions of 1-methoxy-6-nitroindole-3-carbaldehyde 1 Yamada, Koji, Yamada, Fumio, Shiraishi, Takei, Tomioka, Saori, Somei, Masanori 日本複素環化学研究所	11 論文 Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indoles upon reaction of 1-hydroxyindoles with indole in formic … Somei, Masanori, Yamada, Fumio, Hayashi, Toshikatsu, Goto, Aya, Saga, Yoshitomo 日本複素環化学研究所
6 論文 Introduction of nucleophiles or ethyl group to the indole nucleus through nucleophilic substitution and/or radical reactions of 1-methoxyindole-3- and … Yamada, Fumio, Fukui, Yoshikazu, Shinmyo, Daisuke, Somei, Masanori 日本複素環化学研究所	12 論文 Structural determination of a natural alkaloid, 5-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline and the synthesis of the corresponding 8-methoxy compound Yamada, Fumio, Saida, Yoshihiro, Somei, Masanori 日本複素環化学研究所