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Synthetic method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole as well as derivatives of same

A nitrogen heterocycle, 2-D technology, applied in the field of organic synthesis

Active Publication Date: 2018-11-16
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there are few reports on the synthesis of nitrogen-heterocyclic substituted thieno[3,2-d]thiazoles at home and abroad, and the current published literature mainly uses transition metal catalysis

Method used

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  • Synthetic method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole as well as derivatives of same
  • Synthetic method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole as well as derivatives of same
  • Synthetic method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole as well as derivatives of same

Examples

Experimental program
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Effect test

Embodiment 1

[0100] The NMR and mass spectrum data of the product of Example 1 are as follows:

[0101] 1 H NMR (400MHz, CDCl 3 )δ8.74(d, J=6.0Hz, 2H), 8.28(d, J=7.8Hz, 1H), 7.90(d, J=6.1Hz, 2H), 7.85(d, J=8.0Hz, 1H) , 7.56-7.41(m, 2H). 13 C NMR (100MHz, CDCl 3 )δ167.0, 156.7, 150.6, 142.9, 140.7, 132.7, 130.2, 125.7, 125.4, 123.4, 122.0, 120.1. HRMS (ESI) m / z calcd for C 14 h 9 N 2 S 2 + (M+H) + 269.0202, found 269.0205.

Embodiment 2

[0102] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0103] 1 H NMR (400MHz, CDCl 3 )δ8.73(d, J=6.0Hz, 2H), 8.15(d, J=8.1Hz, 1H), 7.89(dd, J=4.7, 1.4Hz, 2H), 7.64(s, 1H), 7.34( d, J=8.1Hz, 1H), 2.52(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ166.8, 156.7, 150.5, 143.3, 140.9, 135.9, 131.8, 127.9, 126.9, 123.4, 121.6, 120.1, 21.63. HRMS (ESI) m / z calcd for C 15 h 11 N 2 S 2 + (M+H) + 283.0358, found 283.0359.

Embodiment 3

[0104] The NMR and mass spectrum data of the product of embodiment 3 are as follows:

[0105] 1 H NMR (400MHz, CDCl 3 )δ8.74(d, J=4.5Hz, 2H), 8.15(d, J=9.0Hz, 1H), 7.90(d, J=5.6Hz, 2H), 7.34(d, J=1.8Hz, 1H) , 7.13(dd, J=8.8, 1.8Hz, 1H), 3.92(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ166.78, 158.25, 156.37, 150.57, 144.41, 140.75, 130.05, 123.97, 122.44, 120.02, 114.37, 106.68, 55.65. HRMS (ESI) m / z calcd for C 15 h 11 N 2 OS 2 + (M+H) + 299.0307, ​​found 299.0304.

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Abstract

The invention mainly relates to a synthetic method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole as well as derivatives of same. In the invention, with oxime ester, methyl nitrogen-heterocyclic ring and sulfur simple substance being raw materials, researching on a three-component cyclization reaction is carried out under promotion effect by an organic solvent, and a benzothiophene multiheterocyclic derivative is synthesized through intermolecular cyclization under a gentle condition. The synthetic method is free of transition metal catalysis and supplies a new approach for synthesizing benzothiophene compounds. The method also has advantages such as simple reaction system, gentle reaction conditions, less reaction equipment, simple experimental operations and above-average yield; and the product is a potential luminescent materials.

Description

technical field [0001] The present invention relates to a synthesis method of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole and its derivatives, in particular to a nitrogen-heterocyclic-substituted benzo[4,5]thieno[3,2-d ] Thiazoles, derivatives and synthesis methods thereof belong to the field of organic synthesis. Background technique [0002] Thieno[3,2-d]thiazoles substituted with nitrogen heterocycles and their derivatives are an important class of functional organic compounds with multifunctional groups and good luminescent properties, because they are widely used in organic synthesis, and are also used in medicine and Materials and other fields have extremely high application value. So far, there are few reports on the synthesis methods of nitrogen-heterocyclic substituted thieno[3,2-d]thiazole compounds at home and abroad, and the current published literature mainly uses transition metal catalysis. Contents of the invention [0003] Therefore, the objec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C07D513/14
CPCC07D513/04C07D513/14
Inventor 黄华文汪倩肖福红邓国军
Owner XIANGTAN UNIV
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