Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives

A technology of high allylamine and derivatives, applied in the field of chemical medicine, can solve the problems of difficult catalysts, unable to realize allylation reaction and the like

Active Publication Date: 2017-12-15
SICHUAN UNIV
View PDF5 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, both of these methods require the use of catalysts or chiral ligands that are extremely difficult to prepare; at the same time, neither of these methods can achieve allylation reactions

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives
  • End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives
  • End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0263] Synthesis of Example 1 (trans)-nitrogen-benzylidene-9 hydrogen-fluorene-9-amine (substrate-1.1-1)

[0264]

[0265] 9H-fluorene-9-amine (English name: 9H-fluoren-9-amine, 1 mmol), benzaldehyde (1 mmol) and Molecular sieves (0.3 g) were stirred in dichloromethane (5 mL) at room temperature for half an hour, then filtered and the solvent removed to give Substrate-1.1-1.

Embodiment 2

[0266]Example 2 Synthesis of (trans)-nitrogen-pyridine-3-methylene-9 hydrogen-fluorene-9-amine (substrate-1.1-2)

[0267]

[0268] 9H-fluorene-9-amine (English name: 9H-fluoren-9-amine, 1 mmol), pyridine-3-formaldehyde (1 mmol) and Molecular sieves (0.3 g) were stirred in dichloromethane (5 mL) at room temperature for half an hour, then filtered and the solvent removed to give Substrate-1.1-2.

[0269] 1 H NMR (400MHz, CDCl 3 )δ:8.94(d,J=2.1Hz,1H),8.80(s,1H),8.66(dd,J=4.8,1.8Hz,1H),8.18(dt,J=7.9,2.0Hz,1H), 7.77 (dd, J=7.6, 1.0Hz, 2H), 7.47–7.37 (m, 5H), 7.31 (td, J=7.4, 1.1Hz, 2H), 5.48 (s, 1H). 13 C NMR (101MHz, CDCl 3 )δ: 160.43, 151.94, 150.68, 144.38, 141.20, 134.96, 131.78, 128.77, 127.66, 125.37, 123.83, 120.36, 74.80. HRMS (DART-TOF) C 19 h 15 N 2 + [M+H] + m / z 271.1234. Melting point: 110-120°C.

Embodiment 3

[0270] Example 3 Synthesis of (trans)-nitrogen-(4-methylthiazole-5-methylene)-9 hydrogen-fluorene-9-amine (substrate-1.1-3)

[0271]

[0272] 9H-fluorene-9-amine (English name: 9H-fluoren-9-amine, 1 mmol), 4-methylthiazole-5-aldehyde (English name: 4-methylthiazole-5-carbaldehyde, 1 mmol) ,and Molecular sieves (03 g) were stirred in dichloromethane (5 mL) at room temperature for half an hour, then filtered and the solvent removed to give Substrate-1.1-3.

[0273] IR (thin film, cm -1 ) 3016, 1619, 1448, 1260, 749. 1 H NMR (400MHz, CDCl 3 )δ:8.88(s,1H),8.72(s,1H),7.74(d,J=7.5Hz,2H),7.43(m,4H),7.31(ddd,J=7.6,7.6,1.2Hz,2H ), 5.46(s,1H), 2.67(s,3H). 13 C NMR (101MHz, CDCl 3 )δ: 155.35, 154.88, 154.01, 144.43, 141.15, 130.93, 128.72, 127.62, 125.38, 120.32, 74.61, 16.01. HRMS (DART-TOF) C 18 h 15 N 2 S + [M+H] + m / z291.0952. Melting point: 166.1~169.0℃.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the field of chemical medicines, and particularly relates to end-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives. In the method, the end-substituted homoallylic amine derivatives are prepared by allowing a 2-aza-allyl anion to participate, in a high regioselectivity manner, an allylation reaction catalyzed by iridium, and by an intramolecular 2-aza-Cope rearrangement reaction. The derivatives can be synthesized efficiently by the method. The method is simple, convenient and feasible. Prepared compounds have extremely high optical purity. The derivatives prepared by the method can be used for preparing Sertraline and Tametraline which are anti-depression medicines and some natural products.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and in particular relates to a terminal-substituted homoallylamine derivative, a preparation method and application thereof. Background technique [0002] Chiral amine structural units widely exist in compounds with important biological activities (such as marketed drugs) and transition metal ligands. Therefore, efficient, universal, and easy-to-use methods for the synthesis of chiral amines have always been a hot research field in synthetic chemistry. Imine, a compound containing a C=N bond, is currently the most commonly used intermediate for the synthesis of chiral amines. Imines can be prepared from the condensation of aldehydes and ketones with primary amines, which are themselves an electrophilic type of compound. Thus, the conversion of imines to chiral amines is usually by reaction with nucleophiles. However, due to the weak electrophilicity of the C=N bonds of general imines, in ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C249/02C07C251/20C07D213/53C07D277/28C07D213/38C07D231/16C07D307/52C07D333/20C07D207/335C07D233/64C07D231/12C07D209/14C07D215/12C07D317/58C07D213/64C07D471/04C07D209/48C07C209/62C07C211/27C07C211/28C07C211/29C07C221/00C07C225/16C07C229/38C07C213/08C07C217/48C07C227/18C07C229/34C07C211/49C07C253/30C07C255/58
CPCC07C209/62C07C211/27C07C211/28C07C211/29C07C211/49C07C213/08C07C217/48C07C221/00C07C225/16C07C227/18C07C229/34C07C229/38C07C249/02C07C251/20C07C253/30C07C255/58C07C269/04C07C269/06C07D207/335C07D209/14C07D209/48C07D213/38C07D213/53C07D213/64C07D215/12C07D231/12C07D231/16C07D233/64C07D277/28C07D307/52C07D317/58C07D333/20C07D471/04C07C251/24C07C251/16C07C271/12C07C211/42
Inventor 钮大文张霞刘捷
Owner SICHUAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com