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METHOD FOR PRODUCING OPTICALLY ACTIVE OXINDOLE COMPOUND AND TRIAZOLIUM SALT USED THEREIN AS CATALYST コモンズ

外国特許コード F160008733
整理番号 NU-651
掲載日 2016年4月28日
出願国 世界知的所有権機関(WIPO)
国際出願番号 2016JP054960
国際公開番号 WO 2016133217
国際出願日 平成28年2月19日(2016.2.19)
国際公開日 平成28年8月25日(2016.8.25)
優先権データ
  • 特願2015-032106 (2015.2.20) JP
発明の名称 (英語) METHOD FOR PRODUCING OPTICALLY ACTIVE OXINDOLE COMPOUND AND TRIAZOLIUM SALT USED THEREIN AS CATALYST コモンズ
発明の概要(英語) The present invention is able to provide a method for stereoselectively introducing an amino group having various substituents into the α-position of an oxindole compound by a single step by having a specific compound (a carbonyl compound such as an oxindole compound) and a specific hydroxyl amine compound or hydrogen peroxide react with each other in the presence of a specific triazolium salt and a specific trihalogenated acetonitrile compound without undergoing a reaction for reductively breaking a nitrogen-nitrogen bond, a nitrogen-oxygen bond or the like of the product. In addition, an amino group having various substituents is able to be stereoselectively introduced into the α-position of another substrate by a single step by means of a similar reaction mechanism. It is preferable that this reaction is carried out in the presence of a base.
特許請求の範囲(英語) [claim1]
1. General system (1A):
[In formula, R, (1) equality or differing, shows the halogen atom or the organic basis.
R (2) shows the hydrogen atom or the organic basis.
R (3) shows the organic basis.
R (4) shows the amino group or hydroxyl group which is possible to be substituted. n shows the integer of the 0-4. ]
So being production method of the optical active chemical compound which is displayed,
General system (2):
[In formula, X (1) shows the halogen atom or the anion of 1 value.
R (5), R (8), R (9) and R (10) equality or differing, it shows the aryl basis which is possible to be substituted.
R (6) shows the primary alkyl group which is possible to be substituted.
R (7) the aliphatic alkyl group which is possible to be substituted or [shikuroarukiru] which is possible to be substituted is shown. ]
So the [toriazoriumu] salt which is displayed and,
General system (3):
CX (2) [3] CN (3)
[In formula, X, (2) equality or differing, shows the halogen atom. ]
So under existing of the [toriharogen] asetonitoriru chemical compound which is displayed,
General system (4A):
[In formula, R (1), R (2), R (3) and n is the same to the description above. ]
So the chemical compound which is displayed and,
General system (5):
R (11) NHOH (5)
[In formula, R (11) the organic basis is shown. ]
So the reaction process which reacts with the hydroxylamine compound or the hydrogen peroxide which is displayed
It has, production method.
[claim2]
2. The aforementioned reaction process, is done under existing of the base, in claim 1 production method of statement.
[claim3]
3. The aforementioned general system (1A) R in it is the amino group (4) may be substituted,
The aforementioned reaction process, are displayed with the aforementioned general system (2) the [toriazoriumu] salt and the general system which the hydroxylamine compound which under existing of the [toriharogen] asetonitoriru chemical compound which is displayed with (3), the aforementioned general system (4A) with is the process which reacts with the chemical compound which is displayed and is displayed with the aforementioned general system (5), in claim 1 or 2 production method of statement.
[claim4]
4. The aforementioned general system (1A) R in (4) is hydroxyl group,
The aforementioned reaction process, are displayed with the aforementioned general system (2) the [toriazoriumu] salt and the general system which under existing of the [toriharogen] asetonitoriru chemical compound which is displayed with (3), the aforementioned general system (4A) with is the process which reacts with chemical compound and the aforementioned hydrogen peroxide which are displayed, in claim 1 or 2 production method of statement.
[claim5]
5. General system (1B):
[In formula, R, (1) equality or differing, shows the halogen atom or the organic basis.
R (11) the organic basis is shown.
R shows the organic basis. n shows the integer of the 0-4. ]
So being production method of the optical active chemical compound which is displayed,
General system (2):
[In formula, X (1) shows the halogen atom or the anion of 1 value.
R (5), R (8), R (9) and R (10) equality or differing, it shows the aryl basis which is possible to be substituted.
R (6) shows the primary alkyl group which is possible to be substituted.
R (7) the aliphatic alkyl group which is possible to be substituted or [shikuroarukiru] which is possible to be substituted is shown. ]
So the [toriazoriumu] salt which is displayed and,
General system (3):
CX (2) [3] CN (3)
[In formula, X, (2) equality or differing, shows the halogen atom. ]
So under existing of the [toriharogen] asetonitoriru chemical compound which is displayed,
General system (4B):
[In formula, R (1), R and n are the same to the description above. ]
So the chemical compound which is displayed and,
General system (5):
R (11) NHOH (5)
[In formula, R (11) the organic basis is shown. ]
So the reaction process which reacts with the hydroxylamine compound which is displayed
It has, production method.
[claim6]
6. The aforementioned reaction process, is done under existing of the base, in claim 5 production method of statement.
[claim7]
7. General system (1C):
[In formula, R, (1) equality or differing, shows the halogen atom or the organic basis.
R (2) shows the hydrogen atom or the organic basis.
R (12) the connected basis of 2 value is shown. n shows the integer of the 0-4. ]
So being production method of the optical active chemical compound which is displayed,
General system (2):
[In formula, X (1) shows the halogen atom or the anion of 1 value.
R (5), R (8), R (9) and R (10) equality or differing, it shows the aryl basis which is possible to be substituted.
R (6) shows the primary alkyl group which is possible to be substituted.
R (7) the aliphatic alkyl group which is possible to be substituted or [shikuroarukiru] which is possible to be substituted is shown. ]
So the [toriazoriumu] salt which is displayed and,
General system (3):
CX (2) [3] CN (3)
[In formula, X, (2) equality or differing, shows the halogen atom. ]
So under existing of the [toriharogen] asetonitoriru chemical compound which is displayed,
General system (4C):
[In formula, R (1), R (2), R (12) and n is the same to the description above.
R (13) the alkyl group is shown. ]
So the chemical compound which is displayed, cyclization reaction process inside the molecule which it cyclizes reacts inside the molecule
It has, production method.
[claim8]
8. Cyclization reaction process inside the aforementioned molecule, is done under existing of the base, in claim 7 production method of statement.
[claim9]
9. General system (2):
[In formula, X (1) shows the halogen atom or the anion of 1 value.
R (5), R (8), R (9) and R (10) equality or differing, it shows the aryl basis which is possible to be substituted.
R (6) shows the primary alkyl group which is possible to be substituted.
R (7) the aliphatic alkyl group which is possible to be substituted or [shikuroarukiru] which is possible to be substituted is shown. ]
So asymmetrical ***.alpha.-amino conversion or the asymmetrical ***.alpha.-hidorokishiru conversion catalyst of the carbonyl compound which consists of the [toriazoriumu] salt which is displayed.
[claim10]
10. As for the aforementioned carbonyl compound,
General system (4A):
[In formula, R, (1) equality or differing, shows the halogen atom or the organic basis.
R (2) shows the hydrogen atom or the organic basis.
R (3) shows the organic basis. n shows the integer of the 0-4. ]
So the chemical compound which is displayed,
General system (4B):
[In formula, R (1) and n is the same to the description above.
R shows the organic basis. ]
So the chemical compound which is displayed, or
General system (4C):
[In formula, R (1), R (2) and n is the same to the description above.
R (12) the connected basis of 2 value is shown.
R (13) the alkyl group is shown. ]
So it is the chemical compound which is displayed, in claim 9 asymmetrical ***.alpha.-amino conversion or the asymmetrical ***.alpha.-hidorokishiru conversion catalyst of the carbonyl compound of statement.
[claim11]
11. General system (2A):
[In formula, PH shows phenyl group.
R (14) 4 - [kurorohueniru] is shown. ]
So the [toriazoriumu] salt which is displayed.
[claim12]
12. General system (1A):
[In formula, R, (1) equality or differing, shows the halogen atom or the organic basis.
R (2) shows the hydrogen atom or the organic basis.
R (3) shows the organic basis.
R (4) shows the amino group or hydroxyl group which is possible to be substituted. n shows the integer of the 0-4. ]
General system (1B):
[In formula, R (1) and n is the same to the description above.
R (11) the organic basis is shown.
R shows the organic basis. ]
Or general system (1C):
[In formula, R (1), R (2) and n is the same to the description above.
R (12) the connected basis of 2 value is shown. ]
So the optical active chemical compound which is displayed.
  • 出願人(英語)
  • ※2012年7月以前掲載分については米国以外のすべての指定国
  • NAGOYA UNIVERSITY
  • 発明者(英語)
  • OOI TAKASHI
  • OHMATSU KOHSUKE
国際特許分類(IPC)
指定国 National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IR IS JP KE KG KN KP KR KZ LA LC LK LR LS LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SA SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW
ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW
EAPO: AM AZ BY KG KZ RU TJ TM
EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN ST TD TG
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