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2-aminobenzo[4,5]thieno[3,2-d]thiazole, and derivative and synthetic method thereof

A 2-d, aminobenzene technology, applied in organic chemistry and other fields

Active Publication Date: 2019-05-03
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are few reports on the synthesis method of 2-aminobenzo[4,5]thieno[3,2-d]thiazole compounds at home and abroad, and the current published literature mainly uses transition metal catalysis

Method used

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  • 2-aminobenzo[4,5]thieno[3,2-d]thiazole, and derivative and synthetic method thereof
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  • 2-aminobenzo[4,5]thieno[3,2-d]thiazole, and derivative and synthetic method thereof

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Experimental program
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Effect test

Embodiment 1

[0099] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0100] 1 H NMR (400MHz, DMSO-d 6 )δ10.51(s, 1H), 7.99-7.96(m, 2H), 7.76(d, J=7.9Hz, 2H), 7.44(t, J=7.4Hz, 1H), 7.38-7.32(m, 3H ), 6.98(t, J=7.3Hz, 1H); 13 C NMR (100MHz, DMSO-d 6 )δ166.5, 150.5, 141.8, 141.3, 130.6, 129.5, 125.3, 124.5, 124.2, 122.1, 121.1, 120.5, 117.6. HRMS (ESI) m / z calcd for C 15 h 11 N 2 S 2 + (M+H) + 283.0358, found 283.0361.

Embodiment 2

[0101] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0102] 1 H NMR (400MHz, DMSO-d 6 )δ10.43(s, 1H), 7.85(d, J=8.0Hz, 1H), 7.75(d, J=7.1Hz, 3H), 7.34(t, J=7.7Hz, 2H), 7.26(d, J=8.1Hz, 1H), 6.97(t, J=7.2Hz, 1H), 2.42(s, 3H); 13 C NMR (100MHz, DMSO-d 6 )δ166.4, 150.4, 142.1, 141.3, 134.1, 129.5, 128.5, 126.7, 123.9, 122.0, 120.8, 119.2, 117.6, 21.5. HRMS (ESI) m / z calcd for C 16 h 13 N 2 S 2 + (M+H) + 297.0515, found 297.0518.

Embodiment 6

[0103] The NMR and mass spectrometry data of embodiment 6 product are as follows:

[0104] 1 H NMR (400MHz, DMSO-d 6 )δ10.48(s, 1H), 8.15(d, J=1.7Hz, 1H), 7.94(d, J=8.5Hz, 1H), 7.74(d, J=7.8Hz, 2H), 7.46(dd, J=8.5, 1.9Hz, 1H), 7.35(t, J=7.9Hz, 2H), 6.98(t, J=7.3Hz, 1H); 13 C NMR (100MHz, DMSO-d 6)δ166.8, 149.7, 143.1, 141.2, 129.5, 129.3, 129.0, 125.6, 123.7, 122.2, 122.1, 121.6, 117.7. HRMS (ESI) m / z calcd for C 15 h 10 ClN 2 S 2 + (M+H) + 316.9968, found 316.9971.

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Abstract

The invention mainly relates to a technical scheme of realizing high-efficiency and green generation of 2-aminobenzo[4,5]thieno[3,2-d]thiazole and derivatives thereof from an oxime ester compound, anisothiocyanate compound and sulfur powder under the combined action of bialkali and dimethyl sulfoxide without the need of a transition metal for catalysis through a one-pot and multi-component process. According to the invention, with oxime ester, phenyl isothiocyanate and elemental sulfur as raw materials, and under the promotion action of bialkali and dimethyl sulfoxide, the research on three-component cyclization reaction is performed, and benzothiophene polyheterocyclic derivatives are synthesized through intermolecular cyclization under mild conditions. The method provided by the invention does not need to use the transition metal for catalysis, provides a novel path for synthesis of benzothiophene compounds, and has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple and convenient experiment operation, medium-to-high yield, etc.

Description

technical field [0001] The invention relates to 2-aminobenzo[4,5]thieno[3,2-d]thiazole, derivatives and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] 2-Aminobenzo[4,5]thieno[3,2-d]thiazole and its derivatives are an important class of organic compounds with multifunctional groups, because they are widely used in organic synthesis, and are also widely used in the fields of medicine and materials. Has a very high application value. So far, there are few reports on the synthesis methods of 2-aminobenzo[4,5]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] Accordingly, the object of the present invention is to provide a 2-aminobenzo[4,5]thieno[3,2-d]thiazole and derivatives thereof. [0004] Another object of the present invention is to provide a synthesis method of 2-aminobenzo[4,5]thieno[3,2-d]thiazole an...

Claims

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Application Information

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IPC IPC(8): C07D513/04C07D513/14
Inventor 黄华文屈中华邓国军肖福红陈善平
Owner XIANGTAN UNIV
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