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A copper-catalyzed tandem cyclization reaction for the construction of n-thiazoline indoles

A technology of thiazoline indole derivatives and indole, applied in the field of fine chemicals, can solve problems such as unreported

Active Publication Date: 2020-04-07
山东博苑医药化学股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are so many methods that can be used to build the indole skeleton, the method for building the N-thiazoline indole skeleton has not been reported at present, and what have is only for the construction of the N-benzothiazoline indole skeleton (Org.Lett .2016, 18(3), 356-359.)

Method used

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  • A copper-catalyzed tandem cyclization reaction for the construction of n-thiazoline indoles
  • A copper-catalyzed tandem cyclization reaction for the construction of n-thiazoline indoles
  • A copper-catalyzed tandem cyclization reaction for the construction of n-thiazoline indoles

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preparation example Construction

[0099] The present invention provides a kind of preparation method of above-mentioned N-thiazoline indole derivative, and this method comprises: in the presence of catalyst, in the presence of ligand, in organic solvent, alkynyl isocyanate represented by formula (II) Thiocyanate and propargyl amine shown in formula (III) carry out serial reaction, obtain the compound shown in formula (I);

[0100]

[0101] The preparation process can be represented by the following route one:

[0102] Route 1:

[0103]

[0104] According to the present invention, the compound shown in formula (II) and formula (III) can carry out concrete selection according to required formula (I), and its R 1 , R 2 , R 3 , R 4 , R 5 As described above, the present invention will not be repeated here.

[0105] Preferably, the molar ratio of the alkynyl isothiocyanate represented by formula (II) to the propargylamine compound represented by formula (III) is 1:0.8-2.0, preferably 1:1-1.5.

[0106] Pre...

Embodiment 1

[0115] Synthesis of 5-methylene-2-(2-phenyl-1H-indole-1)-4,5-dihydrothiazole (I-1)

[0116]

[0117] In a dry Schlenk tube, add the substrate alkynyl phenylisothiocyanate II-1 (0.3mmol, 1.0equiv), propargylamine derivative III-1 (0.45mmol, 1.5equiv), CuI (0.045mmol, 15mol%) ) and dry acetonitrile (3.0 mL). The reaction system was stirred at room temperature for 15 min under an Ar atmosphere, and then stirred at 80° C. for 6 h. After the reaction was completed, the solvent was removed, and the target product I-1 was obtained by silica gel column chromatography. Yellow oil, yield 85%, 1 H NMR (400MHz, CDCl 3 )δ8.06(d,J=8.0Hz,1H),7.59(d,J=7.6Hz,1H),7.51(dd,J=7.6,1.6Hz,2H),7.45–7.37(m,3H), 7.33–7.27(m,1H),7.25–7.20(m,1H),6.66(s,1H),5.19(dd,J=4.4,2.4Hz,1H),5.04(dd,J=4.8,2.8Hz, 1H), 4.98(t, J=2.8Hz, 2H); 13 C NMR (100MHz, CDCl 3 )δ155.1, 147.7, 140.3, 138.1, 132.0, 129.3, 129.0, 128.6, 128.4, 124.0, 122.7, 120.7, 113.4, 107.8, 103.9, 67.2. HRMS (ESI) calcd for C 18 h 15 ...

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Abstract

The invention provides an N-thiazoline indole derivative and a preparation method thereof. The N-thiazoline indole derivative is a compound represented by a formula (I) shown in the description. The preparation method of the N-thiazoline indole derivative comprises the step of subjecting alkynyl isothiocyanate represented by a formula (II) shown in the description and alkynyl propylamine represented by a formula (III) shown in the description to a cascade reaction, thereby obtaining the compound represented by the formula (I).

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to N-thiazoline indole derivatives and a preparation method thereof. Background technique [0002] The indole ring is a very important structural basis and widely exists in many natural products, drug molecules, pesticide molecules and functional materials. Due to its unique role, a large number of methodologies for the construction of indole derivatives have emerged in the past century, such as the most classic Fischer indole synthesis method, and the most common metal-catalyzed cyclization reactions and C-H bond activation. way to construct the indole skeleton. Although there are so many methods that can be used to build the indole skeleton, the method for building the N-thiazoline indole skeleton has not been reported at present, and what have is only for the construction of the N-benzothiazoline indole skeleton (Org.Lett .2016, 18(3), 356-359.). Considering ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04
CPCC07D417/04
Inventor 汪清民宋红健谢佳林刘玉秀李成林于国清
Owner 山东博苑医药化学股份有限公司