TOP > 外国特許検索 > Process for producing nitrogenous 5-membered cyclic compound

Process for producing nitrogenous 5-membered cyclic compound

外国特許コード F110003811
整理番号 E07609WO
掲載日 2011年7月5日
出願国 アメリカ合衆国
出願番号 59213905
公報番号 20070191614
公報番号 7705161
出願日 平成17年2月21日(2005.2.21)
公報発行日 平成19年8月16日(2007.8.16)
公報発行日 平成22年4月27日(2010.4.27)
国際出願番号 JP2005003236
国際公開番号 WO2005085204
国際出願日 平成17年2月21日(2005.2.21)
国際公開日 平成17年9月15日(2005.9.15)
優先権データ
  • 特願2004-066434 (2004.3.9) JP
  • 2005WO-JP03236 (2005.2.21) WO
発明の名称 (英語) Process for producing nitrogenous 5-membered cyclic compound
発明の概要(英語) (US7705161)
A method of the intramolecular and intermolecular cyclization of an N-acylhydrazone for obtaining a pyrazoline skeleton or pyrazolidine skeleton under ordinary conditions with high stereoselectivity and in high yield.
An N-acylhydrazone represented by the following formula (I): (wherein R1 and R2 are the same or different and each represents hydrogen or a hydrocarbon group and Ar represents an optionally substituted aromatic hydrocarbon group) is converted to an N-acylpyrazoline derivative with high stereoselectivity in the presence of a Lewis acid catalyst or asymmetric Lewis acid catalyst.
特許請求の範囲(英語) [claim1]
1. A process for intramolecular cyclization of an N-acylhydrazone which comprises reacting an N-acylhydrazone represented by the following formula (I)

wherein R1 and R2 are the same or different and each represents a hydrogen atom or a hydrocarbon group, and Ar represents an optionally substituted aromatic hydrocarbon group, with a Lewis acid catalyst to obtain an N-acylpyrazoline derivative represented by the following formula (II)

wherein R1, R2 and Ar have the same meanings as indicated above.
[claim2]
2. A process according to claim 1 wherein the Lewis acid catalyst is scandium triflate.
[claim3]
3. A process for asymmetric intramolecular cyclization of an N-acylhydrazone which comprises reacting an N-acylhydrazone represented by the following formula (I)

wherein R1 and R2 are the same or different and each represents a hydrogen atom or a hydrocarbon group, and Ar represents an optionally substituted aromatic hydrocarbon group, with an asymmetric Lewis acid catalyst, which can be obtained by mixing a zirconium alkoxide or zirconium dialkoxide dihalide represented by the following formula (III)
ZrP2Q2 (III)
wherein P represents an alkoxy group, and Q represents an alkoxy group or a halogen atom, and a binaphthol derivative represented by the following formula (IV)

wherein X represents a hydrogen atom, a halogen atom, a hydrocarbon group or a perfluoroalkyl group; Y represents a hydrogen atom, a halogen atom, a hydrocarbon group or a perfluoroalkyl group; and X and Y may be the same, to obtain an optically active N-acylpyrazoline derivative represented by the following formula (II')

wherein R1, R2 and Ar have the same meanings as indicated above.
[claim4]
4. A process for asymmetric intermolecular cyclization of an N-acylhydrazone which comprises reacting an N-acylhydrazone represented by the following formula (V)

wherein R3 represents an optionally substituted hydrocarbon group and Ar represents an optionally substituted aromatic hydrocarbon group, with an olefinic compound represented by the following formula (VI)

wherein R4 and R5 are the same or different and each represents a hydrogen atom or a substituent selected from the group consisting of hydrocarbon group, alkoxy group and alkylthio group and at least one of R4 and R5 is other than a hydrogen atom, in the presence of an asymmetric Lewis acid catalyst, obtained by mixing a zirconium alkoxide or zirconium dialkoxide dihalide represented by the following formula (III)
ZrP2Q2 (III)
wherein P represents an alkoxy group and Q represents an alkoxy group or a halogen atom, and a binaphthol derivative represented by the following formula (IV)

wherein X represents a hydrogen atom, a halogen atom, a hydrocarbon group or a perfluoroalkyl group, and Y represents a hydrogen atom, a halogen atom, a hydrocarbon group or a perfluoroalkyl group and X and Y may be the same, to obtain an optically active N-acylpyrazolidine derivative represented by the following formula (VII)

wherein R3 to R5 and Ar have the same meanings as indicated above.
  • 発明者/出願人(英語)
  • KOBAYASHI SHU
  • YAMASHITA YASUHIRO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
ライセンスをご希望の方、特許の内容に興味を持たれた方は、問合せボタンを押してください。

PAGE TOP

close
close
close
close
close
close