Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivants

A compound and cyclization reaction technology, applied in the direction of organic chemistry, can solve the problems that cannot be applied to the synthesis of isoquinoline derivatives, and achieve high catalytic activity and selectivity, simple reaction operation, and strong universality

Active Publication Date: 2014-05-28
TSINGHUA UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these catalytic synthesis methods established by Larock et al. cannot be applied to the synthesis of isoquinoline derivatives containing substituents at the 1-position

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
  • Method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivants
  • Method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivants
  • Method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivants

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0052] Wherein, the preparation method of the compound shown in formula II is as follows: the compound shown in formula a, the compound shown in formula b, PdCl 2 (PPh 3 ) 2 , CuI, tetrahydrofuran and triethylamine are mixed in an inert atmosphere to react, and the compound shown in formula II is obtained after the reaction is completed. Compound shown in formula a, compound shown in formula b, PdCl 2 (PPh 3 ) 2 , CuI, tetrahydrofuran and triethylamine are 1mmol: 11mmol: 0.01mmol: 0.02mmol: 2mL: 1mL; in the reaction step, the temperature is 60°C and the time is 5 hours; the method also includes: After completion, the mobile phase was a mixture of ethyl acetate and petroleum ether with a volume ratio of 2:100 for column chromatography to obtain the target product.

[0053]

[0054] Formula a Formula b

[0055] In formula a and formula b, R 1 , R 2 and R 3 The definition is the same as before.

Embodiment 1

[0057] Weigh CuSO 4 Add 16mg (0.1mmol), 206mg (1mmol) of o-phenylethynyl benzaldehyde, 120mg (2mmol) of urea and 2mL toluene into a 25-mL glass reaction tube with a cover, replace the air in the reaction tube with nitrogen, and then seal the reaction tube , put the reaction tube in an oil bath and heat it to 120°C, stir and keep warm for 12 hours, then cool to room temperature to obtain the target product 3-phenylisoquinoline provided by the present invention. Reaction result: the isolated target product 3-phenylisoquinoline was weighed, and the isolated yield of the product was calculated to be 79%. figure 1 with figure 2 The hydrogen spectrum and carbon spectrum of the target product 3-phenylisoquinoline prepared in this example are shown respectively. It can be seen from the figure that the compound has a correct structure and is the target product.

Embodiment 2

[0059] Weigh CuSO 4 16mg (0.1mmol), o-ethynyl benzaldehyde 130mg (1mmol), urea 120mg (2mmol) and 2mL toluene were added in a 25-mL glass reaction tube with a cover, the air in the reaction tube was replaced with nitrogen, and then the reaction tube was sealed. Put the reaction tube in an oil bath and heat to 120°C, stir and keep warm for 12 hours, then cool to room temperature to obtain the target product isoquinoline provided by the present invention. Reaction result: the isolated target product isoquinoline was weighed, and the isolated yield of the product was calculated to be 23%. image 3 with Figure 4 The hydrogen spectrum and carbon spectrum of the target product isoquinoline prepared in this example are respectively, as can be seen from the figure, the compound has a correct structure and is the target product.

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

No PUM Login to View More

Abstract

The invention discloses a method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivants. The method comprises the following steps that: a substituted adjacent acyl aryne compound shown in formula II, urea and a catalyst are mixed uniformly to be cyclized, and the compound shown in the formula I is obtained after reaction. In the method, copper salt is used as the catalyst. The cheap, safe and easy-to-get catalyst is adopted in the method, the reaction condition is simple, convenient and environment-friendly, simultaneously the catalyst system shows high efficiency and high selectivity, and the method has an important application value.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical products, and relates to a method for preparing polysubstituted isoquinoline and heterocyclic pyridine derivatives. Background technique [0002] Isoquinolines and heterocyclopyridines are very important alkaloids that widely exist in natural products. Because of its important physiological and biological activities, it is often used as the skeleton structure of some drug molecules [Selected papers: (a) Dzierszinski, F.; Coppin, A.; Mortuaire, M.; Dewally, E.; Slomianny, C.; Ameisen, J.-C.; DeBels, F.; Tomavo, S. Antimicrob. Agents Chemother. 2002, 46, 3197. (b) Kletsas, D.; Li, W.; Han, Z.; Papadopoulos, V. Biochem. Pharmacol. 2004, 67, 1927]. In addition, isoquinolines and heterocyclic pyridines are often used as chiral ligands for transition metal catalysts [Selected papers: (a) Durola, F.; Sauvage, J.-P.; Wenger, O.S.Chem.Commun. 2006, 171.(b) Lim, C.W.; Tissot,...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/02C07D495/04C07D471/04
Inventor 华瑞茂居佳
Owner TSINGHUA UNIV