Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE OXINDOLE COMPOUND AND TRIAZOLIUM SALT USED THEREIN AS CATALYST
Document Type and Number:
WIPO Patent Application WO/2016/133217
Kind Code:
A1
Abstract:
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.
Inventors:
OOI TAKASHI (JP)
OHMATSU KOHSUKE (JP)
OHMATSU KOHSUKE (JP)
Application Number:
PCT/JP2016/054960
Publication Date:
August 25, 2016
Filing Date:
February 19, 2016
Export Citation:
Assignee:
NAT UNIV CORP NAGOYA UNIV (JP)
International Classes:
C07D209/34; B01J31/02; C07C227/06; C07C229/50; C07D209/36; C07D249/06; C07D487/10; C07B53/00; C07B61/00
Foreign References:
| JP2012082155A | 2012-04-26 |
Other References:
MARI KIYOKAWA ET AL.: "1C3-10 ''1,2,3-Triazolium Cation no Anion Ninshikino o Riyo shita Chiral Yuki Bunshi Shokubai no Sekkei to Kino Soshutsu", THE 91ST ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN IN SPRING (2011) KOEN YOKOSHU IV, 11 March 2011 (2011-03-11), pages 1270, ISSN: 0285-7626
OHMATSU, K. ET AL.: "Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2- Disubstituted Aziridines with 3-Substituted Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 135, no. 50, 2013, pages 18706 - 18709, ISSN: 0002-7863
OHMATSU, K. ET AL.: "Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion- Recognition Ability: Application to Asymmetric Alkylation of Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 5, 2011, pages 1307 - 1309, ISSN: 0002-7863
OHMATSU, K. ET AL.: "Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 21, 2012, pages 8794 - 8797, ISSN: 0002-7863
TOLSTOY, P. ET AL.: "Synthesis of Enantiomerically Enriched 3-Amino-2-oxindoles through a Palladium-Mediated Asymmetric Intramolecular Arylation of alpha-Ketimino Amides", ORGANIC LETTERS, vol. 14, no. 18, 2012, pages 4810 - 4813, ISSN: 1523-7052
GUO, Q.-X. ET AL.: "Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 7, 2012, pages 3589 - 3594, ISSN: 0022-3263
PULEO, L. ET AL.: "Synthesis and pharmacological evaluation of indolinone derivatives as novel ghrelin receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 18, 2012, pages 5623 - 5636, XP028938215, ISSN: 0968-0896, DOI: doi:10.1016/j.bmc.2012.07.018
ISHIMARU, T. ET AL.: "Lewis Acid-Catalyzed Enantioselective Hydroxylation Reactions of Oxindoles and beta-Keto Esters Using DBFOX Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 51, 2006, pages 16488 - 16489, ISSN: 0002-7863
ZHONG, F. ET AL.: "Enantioselective Construction of 3-Hydroxy Oxindoles via Decarboxylative Addition of beta-Ketoacids to Isatins", ORGANIC LETTERS, vol. 14, no. 15, 2012, pages 4018 - 4021, ISSN: 1523-7052
SUH, C. W. ET AL.: "Enantioselective decarboxylative aldol addition of beta-ketoacids to isatins catalyzed by binaphthyl-modified organocatalyst", TETRAHEDRON LETTERS, vol. 54, no. 28, 2013, pages 3651 - 3654, XP028561937, ISSN: 0040-4039, DOI: doi:10.1016/j.tetlet.2013.04.132
RAJKUMAR, V. ET AL.: "Unactivated Norbornenes in [3+2]Cycloadditions: Remarkably Stereo- controlled Entry into Norbornane-Fused Spirooxindolopyrrolidines, Spiro-1,3- indandionolylpyrrolidines, and Spirooxindolopyrrolizidines", SYNLETT, vol. 23, no. 4, 2012, pages 549 - 556, ISSN: 0936-5214
LIN, X. ET AL.: "Model studies on total synthesis of the chartellines, spirocyclic beta- lactam alkaloids from a marine bryozoan", TETRAHEDRON LETTERS, vol. 42, no. 14, 2001, pages 2631 - 2633, XP004231627, ISSN: 0040-4039, DOI: doi:10.1016/S0040-4039(01)00270-2
BENATI, L. ET AL.: "Radical Chain Reactions of alpha-Azido-beta-keto Esters with Tributyltin Hydride. A Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 64, no. 21, 1999, pages 7836 - 7841, XP002700804, ISSN: 0022-3263, DOI: doi:10.1021/JO990837G
PACCANI, R. R. ET AL.: "Toward a Stable a- Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 4, 2012, pages 1738 - 1748, ISSN: 0022-3263
HIROSHI YAMANAKA ET AL.: "1 General aspects of the preparation of optically active compounds", KIKAN KAGAKU SOSETSU NO.6, 1989 RESOLUTION OF OPTICAL ISOMERS, 10 June 1999 (1999-06-10), pages 2 - 14, XP008146717
OHMATSU, K. ET AL.: "Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2- Disubstituted Aziridines with 3-Substituted Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 135, no. 50, 2013, pages 18706 - 18709, ISSN: 0002-7863
OHMATSU, K. ET AL.: "Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion- Recognition Ability: Application to Asymmetric Alkylation of Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 5, 2011, pages 1307 - 1309, ISSN: 0002-7863
OHMATSU, K. ET AL.: "Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 21, 2012, pages 8794 - 8797, ISSN: 0002-7863
TOLSTOY, P. ET AL.: "Synthesis of Enantiomerically Enriched 3-Amino-2-oxindoles through a Palladium-Mediated Asymmetric Intramolecular Arylation of alpha-Ketimino Amides", ORGANIC LETTERS, vol. 14, no. 18, 2012, pages 4810 - 4813, ISSN: 1523-7052
GUO, Q.-X. ET AL.: "Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 7, 2012, pages 3589 - 3594, ISSN: 0022-3263
PULEO, L. ET AL.: "Synthesis and pharmacological evaluation of indolinone derivatives as novel ghrelin receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 18, 2012, pages 5623 - 5636, XP028938215, ISSN: 0968-0896, DOI: doi:10.1016/j.bmc.2012.07.018
ISHIMARU, T. ET AL.: "Lewis Acid-Catalyzed Enantioselective Hydroxylation Reactions of Oxindoles and beta-Keto Esters Using DBFOX Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 51, 2006, pages 16488 - 16489, ISSN: 0002-7863
ZHONG, F. ET AL.: "Enantioselective Construction of 3-Hydroxy Oxindoles via Decarboxylative Addition of beta-Ketoacids to Isatins", ORGANIC LETTERS, vol. 14, no. 15, 2012, pages 4018 - 4021, ISSN: 1523-7052
SUH, C. W. ET AL.: "Enantioselective decarboxylative aldol addition of beta-ketoacids to isatins catalyzed by binaphthyl-modified organocatalyst", TETRAHEDRON LETTERS, vol. 54, no. 28, 2013, pages 3651 - 3654, XP028561937, ISSN: 0040-4039, DOI: doi:10.1016/j.tetlet.2013.04.132
RAJKUMAR, V. ET AL.: "Unactivated Norbornenes in [3+2]Cycloadditions: Remarkably Stereo- controlled Entry into Norbornane-Fused Spirooxindolopyrrolidines, Spiro-1,3- indandionolylpyrrolidines, and Spirooxindolopyrrolizidines", SYNLETT, vol. 23, no. 4, 2012, pages 549 - 556, ISSN: 0936-5214
LIN, X. ET AL.: "Model studies on total synthesis of the chartellines, spirocyclic beta- lactam alkaloids from a marine bryozoan", TETRAHEDRON LETTERS, vol. 42, no. 14, 2001, pages 2631 - 2633, XP004231627, ISSN: 0040-4039, DOI: doi:10.1016/S0040-4039(01)00270-2
BENATI, L. ET AL.: "Radical Chain Reactions of alpha-Azido-beta-keto Esters with Tributyltin Hydride. A Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 64, no. 21, 1999, pages 7836 - 7841, XP002700804, ISSN: 0022-3263, DOI: doi:10.1021/JO990837G
PACCANI, R. R. ET AL.: "Toward a Stable a- Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 4, 2012, pages 1738 - 1748, ISSN: 0022-3263
HIROSHI YAMANAKA ET AL.: "1 General aspects of the preparation of optically active compounds", KIKAN KAGAKU SOSETSU NO.6, 1989 RESOLUTION OF OPTICAL ISOMERS, 10 June 1999 (1999-06-10), pages 2 - 14, XP008146717
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
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