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1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound and preparation method thereof

A compound, 2-d technology, applied in the direction of organic chemistry, can solve the problems of difficulty in the synthesis of macrocyclic compounds, cumbersome reaction steps, etc., and achieve the effects of wide substrate applicability, simple reaction operation, and high yield

Inactive Publication Date: 2020-07-24
SHENZHEN POLYTECHNIC
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because of the unfavorable factors of entropy and intermolecular forces, the synthesis of macrocycles is difficult
In 2015, Mr. Karthikeyan's research group developed a multi-component reaction catalyzed by L-proline to efficiently synthesize pyrazolo[3,4-e][1,4]thiazepine derivatives (An Afficient L -ProlineCatalyzed Synthesis of Pyrazolo[3,4-e][1,4]thiazepine Derivatives and Theirin Vitro Cytotoxicity Studies, A. Srikanth, S. Sarveswari, V. Vijayakumar, P. Gridharan and S. Karthikeyan, Med. Chem. Res .,2015,24,553), the reaction steps are relatively cumbersome

Method used

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  • 1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound and preparation method thereof
  • 1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound and preparation method thereof
  • 1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0026] The reaction formula of embodiment 1, the compound II-1 and compound III-1 and the product I-1 structure of specific use are shown in the following formula, and experiments show that the preferred organic solvent of the present invention is dichloromethane, and the highest yield of its reaction product is 87%, the best molar ratio of raw materials is compound II: compound III=1.2:1.0, when the equivalent value of compound II increases to 1.5 equivalents, the yield of the corresponding reaction decreases, and the optimal concentration of the solution is 0.1M .

[0027]

[0028] The specific experimental steps are: 91mg (0.36mmol, 1.2eq) of compound II-1 and 52mg (0.30mmol, 1.0eq) of compound III-1 were dissolved in 3mL of dichloromethane, heated to 65°C for reaction. The disappearance of the reactant III-1 was monitored by thin-layer chromatography, and the reaction mixture was rotary-evaporated under the reduced pressure of the water pump to remove the solvent dichlo...

Embodiment 2

[0033] The structures of other relevant starting materials for the preparation of compound I-2 to compound I-7 are as follows:

[0034]

[0035] The chemical structures and data characterizations of compounds 1-2 to 1-7 of the present invention:

[0036]

[0037] Product Ⅰ-2 (Formula E) was a yellow oil with a yield of 63%. 1 H NMR (400MHz, (CD 3 ) 2 CO)δ6.42(dd,J=2.6,1.0Hz,1H),6.02–5.92(m,3H),5.53(dd,J=9.4,5.4Hz,1H),5.44–5.38(m,1H), 5.37–5.31(m,2H),5.22(dq,J=10.4,1.2Hz,1H),4.63(dt,J=5.6,1.4Hz,2H),4.23–4.10(m,1H),3.77(s, 3H), 3.72(s, 3H), 2.62(dt, J=17.2, 2.6Hz, 1H); 13 C NMR (100MHz, (CD 3 ) 2 CO)δ165.2(2C),164.4,157.7,145.2,133.4,128.0,125.8,123.9,120.2,118.2,108.2,107.6,65.5,57.5,53.4,53.0,36.4; ESI-HRMS m / z calcd for C 18 h 19 NO 6 S[M+H] + 378.1006,found 378.1012.

[0038] Product Ⅰ-2 (Formula Z) was a yellow oil with a yield of 11%. 1 H NMR (400MHz, (CD 3 ) 2 CO) δ6.19(d,J=7.6Hz,1H),6.16(s,1H),6.08–5.92(m,2H),5.38–5.28(m,3H),5.22(dq,J=10.4,1.2 Hz,1H)...

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Abstract

The invention mainly aims to provide a 1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound and a preparation method thereof. According to the method, the 1, 10a-dihydro-2H-pyridine [1, 2-d][1, 4] thiazepine compound can be efficiently synthesized through reaction of sulfur-containing onium salt and allene at 65 DEG C only under the condition that dichloromethane is used as a solvent without participation of other reagents. The invention also provides a preparation method of the 1, 10a-dihydro-2H-pyridine [1, 2-d] [1, 4] thiazepine compound. Other reaction reagents do not need to beadded, an aza-six-membered ring and seven-membered ring skeleton can be simply constructed and is expected to be applied to synthesis work of drug molecules, reaction raw materials are easy to obtain, reaction operation is simple, other noble metal catalysts do not need to be added, aftertreatment is convenient, substrate applicability is wide, the yield is generally very high, and inert gas protection is not needed in the preparation process. The reaction conditions are mild, the reaction can be quickly and smoothly carried out at 65 DEG C and large-scale preparation is easy.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to 1,10a-dihydro-2H-pyridine[1,2-d][1,4]thiazepine compounds and a preparation method thereof. Background technique [0002] Nitrogen and sulfur elements widely exist in nature and living organisms. The representative nitrogen-containing compounds are natural organic alkaloids, which play an extremely important role in the field of medicine; sulfur-containing compounds are widely used in materials, medicines and even food middle. Organosulfur compounds occupy an important position in organic chemistry due to their excellent properties. Therefore, efforts have been devoted to developing efficient methods for introducing sulfur into organic frameworks. The seven-membered ring system skeleton exists in many natural products and drug molecular skeletons, for example, midazolam, alprazolam and triazolam are tricyclic 1,4-benzodiazepines fused with imidazole and triazole, known as Psy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 程斌张昕平李慧李运通汪太民贺一轩翟宏斌
Owner SHENZHEN POLYTECHNIC
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