Synthesis method of benzo[d]pyrrolo[2,1-b]thiazole

A synthesis method and pyrrole technology, applied in organic chemistry and other directions, can solve the problems of small expansion range of substrates, difficult to obtain raw materials, harsh reaction conditions, etc., and achieve a large expansion range of substrates, reaction conditions are green and pollution-free, and raw materials are easily available. Effect

Inactive Publication Date: 2017-06-20
YANGZHOU UNIV
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Problems solved by technology

[0004] At present, the synthesis of benzothiazolopyrrole compounds has not been reported in the literature, and the existing reports only involve the synthesis of part of the ring structure, and there are some shortcomings, such as the expansion range of the substrate is small, the structure is simple, the raw materials are not easy to obtain, and the reaction conditions are relatively low. Harsh, low yield, etc.

Method used

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  • Synthesis method of benzo[d]pyrrolo[2,1-b]thiazole
  • Synthesis method of benzo[d]pyrrolo[2,1-b]thiazole
  • Synthesis method of benzo[d]pyrrolo[2,1-b]thiazole

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Comparison scheme
Effect test

Embodiment 1

[0023] Example 1, to prepare (3-nitro-2-phenylbenzo[ d ]pyrrolo[2,1- b ] Thiazol-1-yl) (p-tolyl) ketone is example, and its reaction formula and preparation method are as follows:

[0024]

[0025] Add 0.1351g (1.0mmol) benzothiazole, 0.2134g (1.0mmol) 4-methyl-α-bromoacetophenone and 10mL dry acetonitrile to a 50mL round bottom flask, stir and react at 50°C for 12 hours, evaporate acetonitrile. Then add 0.1776g (1.2mmol) 2-phenylnitroene, 0.1200g (1.2mmol) E 3 tN and 10mL dry ethanol, stirred at room temperature for 6 hours, then added 0.5925g (2.5mmol) 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), heated to reflux and stirred for 6 hours. The solvent was concentrated and evaporated on a rotary evaporator, washed with 95% ethanol, and suction filtered to obtain the crude product, which was purified and separated by silica gel column chromatography (the mixing volume ratio of ethyl acetate and petroleum ether was 1:3) to obtain pure (3- Nitro-2-phenylbenzo[ d ]pyrrolo...

Embodiment 2

[0027] Example 2, to prepare (2-(4-methoxyphenyl)-3-nitrobenzo[ d ]pyrrolo[2,1- b ]thiazol-1-yl) (p-tolyl) as an example, its preparation method is as follows:

[0028]

[0029] In Example 1, the 2-phenylnitroalkene used is replaced with 2-(4-methoxy)phenylnitroalkene in an equimolar amount, and other steps are the same as in Example 1 to obtain (2-(4- Methoxyphenyl)-3-nitrobenzo[ d ]pyrrolo[2,1- b ]thiazol-1-yl) (p-tolyl), its isolated yield is 88%, and the structural characterization data are as follows:

[0030] 1 H NMR (400 MHz, DMSO- d 6 ) δ: 8.26~8.24 (m, 1H, ArH), 7.70 ~7.68 (m, 1H,ArH), 7.63 (d, J = 8.0 Hz, 2H, ArH), 7.57~7.52 (m, 2H, ArH), 7.19 (d, J = 8.0Hz, 2H, ArH), 7.10 (d, J = 8.0 Hz, 2H, ArH), 6.73 (d, J = 8.4 Hz, 2H, ArH),3.67 (s, 3H, OCH 3 ), 2.26 (s, 3H, CH 3 ); 13 C NMR (150 MHz, DMSO- d 6 ) Δ: 186.7,159.0, 144.2, 139.5, 134.1, 133.7, 131.9, 130.5, 130.0, 128.9, 127.2,126.0, 125.1, 124.5, 122.9, 112.9, 55.0, 21.1; IR (KBR) υ υ :2926, 1615,...

Embodiment 3

[0031] Example 3, to prepare (2-(3-methoxyphenyl)-3-nitrobenzo[ d ]pyrrolo[2,1- b ]thiazol-1-yl) (p-tolyl) as an example, its preparation method is as follows:

[0032]

[0033] In Example 1, the 2-phenylnitroalkene used is replaced with 2-(3-methoxy)phenylnitroalkene in an equimolar amount, and other steps are the same as in Example 1 to obtain (2-(3- Methoxyphenyl)-3-nitrobenzo[ d ]pyrrolo[2,1- b ]thiazol-1-yl) (p-tolyl), its isolated yield is 89%, and the structural characterization data are as follows:

[0034] 1 H NMR (400 MHz, DMSO- d 6 ) δ: 8.27~8.24 (m, 1H, ArH), 7.71~7.69 (m, 1H,ArH), 7.65 (d, J = 8.0 Hz, 2H, ArH), 7.58~7.53 (m, 2H, ArH), 7.10~7.06 (m,3H, ArH), 6.86~6.80 (m, 2H, ArH), 6.75~6.72 (m, 1H, ArH), 3.64 (s, 3H, OCH 3 ),2.26 (s, 3H, CH 3 ); 13 C NMR (150 MHz, DMSO- d 6 ) Δ: 186.6, 158.1, 144.3, 139.4,134.2, 133.7, 131.3, 130.5, 129.9, 128.8, 127.2, 126.1, 124.7,123.0, 115.9, 113.8, 55.0, 21.1; : 2933, 1636, 1597, 1535, 1496, 1467, 1395, 1342,...

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Abstract

The invention relates to a synthesis method of benzo[d]pyrrolo[2,1-b]thiazole and belongs to the technical field of organic synthesis. The synthesis method comprises the following step: in acetonitrile, mixing benzothiazole and bromide and performing reaction to obtain N-benzoyl methylbenzothiazole bromide; under the existence of ethanol and an alkaline catalyst, mixing the N-benzoyl methylbenzothiazole bromide and nitroolefin and performing addition reaction to obtain a tetrahydro-benzo[d]pyrrolo[2,1-b]thiazole compound; and mixing the tetrahydro-benzo[d]pyrrolo[2,1-b]thiazole compound and excessive antioxidants, heating, performing refluxing reaction, and performing silica-gel column chromatography to obtain the benzo[d]pyrrolo[2,1-b]thiazole. The synthesis method of the benzo[d]pyrrolo[2,1-b]thiazole is easily available in raw material, green in reaction condition, rapid in reaction and large in substrate expanding range, and does not need metal catalysts to participate.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] The pyrrole ring structure skeleton is closely related to people's life, and it widely exists in many natural products and medicines. For example, indigo is a natural dye widely used in the coloring of medicine, food and daily chemical products; β-indole acetic acid, as a plant hormone, can control the growth of plants, etc. As the basic skeleton of a class of nitrogen-containing heterocyclic drugs with a wide range of properties, pyrrole ring derivatives have prompted more people to pay more attention to pyrrole ring compounds (Minetto, G; Raveglia, L F; Taddei, M. Microwave-Assisted Paal- Knorr Reaction. A Rapid Approach to Substituted Pyrroles and Furans[J]. Org. Lett ., 2004, 6 (3): 389-392). [0003] Many derivatives with pyrrole structure have significant biological activity. For example: Lukianol A shows activity against human epidermal carcinom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 孙晶金功颜朝国韩莹
Owner YANGZHOU UNIV
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