Allene thiocyanide derivative and synthesis method thereof

A technology of allene thiocyanide and thiocyanide, which is applied in the direction of organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve the problems of narrow substrate range, cumbersome operation, and low safety, and achieve easy preparation, The operation method is simple and the yield is good

Active Publication Date: 2018-08-21
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthesis methods of allene thiocyanides have the disadvantages of requiring highly toxic reagents, step-by-step reactions, cumbersome operation, low safety, high cost, and narrow substrate range.

Method used

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  • Allene thiocyanide derivative and synthesis method thereof
  • Allene thiocyanide derivative and synthesis method thereof
  • Allene thiocyanide derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

[0049] KBr (0.15mmol), AgSCF 3(0.15mmol) was added in acetonitrile (2mL), 4-(benzyloxy)-1-phenylbut-2-yn-1-amine (0.1mmol) was dissolved in acetonitrile (2mL), and then dissolved in acetonitrile ( 2 mL) of 4-(benzyloxy)-1-phenylbut-2-yn-1-amine (0.1 mmol) was added dropwise to the reaction system, and the reaction system was at room temperature. After the dropwise addition, stirred for 1 hour , and the solvent was removed under reduced pressure to obtain a crude product, which was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:10) to obtain a pure product. Its structure is shown in formula (2-1). The yield was 80%. nuclear magnetic resonance 1 H NMR, 13 C NMR spectrum as figure 1 shown. 1 HNMR (400MHz, CDCl3) δ7.40–7.26 (m, 10H), 6.67 (s, 1H), 4.60 (q, J=11.7Hz, 2H), 4.35 (d, J=2.1Hz, 2H). 13 C NMR (101MHz, CDCl 3 )δ 203.44, 136.95, 131.17, 129.08, 128.60, 128.16, 128.08, 128.05, 110.03, 102.12, 95.85, 72.49, 69.45.

[0050] HRMS...

Embodiment 2

[0052]

[0053] 1-(4-Chlorophenyl)-4-(naphthalen-2-yloxy)but-2-yn-1-amine was dissolved in acetonitrile (2 mL). KBr (0.15mmol), AgSCF 3 (0.15mmol), was added to acetonitrile (2mL), then 1-(4-chlorophenyl)-4-(naphthalene-2-yloxy)but-2-yne dissolved in acetonitrile (2.0ml) -1-Amine (0.1 mmol) was added dropwise to the reaction system, and the reaction system was at room temperature. After the dropwise addition, the reaction system was stirred for 1 hour, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:10) to obtain a pure product. Its structure is shown in formula (2-2). The yield was 81%. nuclear magnetic resonance 1 HNMR, 13 C NMR spectrum as figure 2 shown. 1 H NMR (400MHz, CDCl3) δ7.76 (t, J = 9.3Hz, 2H), 7.61 (d, J = 8.1Hz, 1H), 7.41 (dt, J = 14.9, 6.9Hz, 2H), 7.16 (dd ,J=17.9,7.8Hz,4H),7.07(d,J=8.4Hz,2H),6.64(s,1H),5.02(qd,J=12.8,2.1Hz,2...

Embodiment 3

[0056]

[0057] 1-(4-Methoxyphenyl)-4-(naphthalen-2-yloxy)but-2-yn-1-amine was dissolved in acetonitrile (2 mL). KBr (0.15mmol), AgSCF 3 (0.15mmol), was added to acetonitrile (2mL), then 1-(4-chlorophenyl)-4-(naphthalene-2-yloxy)butan-2 dissolved in (2.0ml) in acetonitrile -Alkyne-1-amine (0.1 mmol) was added dropwise to the reaction system, and the reaction system was at room temperature. After the dropwise addition was completed, it was stirred for 1 hour, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:10) to obtain a pure product. Its structure is shown in formula (2-3). The yield was 82%. nuclear magnetic resonance 1 HNMR, 13 C NMR spectrum as image 3 shown. 1 H NMR (400MHz, CDCl3) δ7.75 (dd, J = 8.0, 5.7Hz, 2H), 7.59 (d, J = 8.0Hz, 1H), 7.49–7.31 (m, 2H), 7.26–7.04 (m, 3H), 6.80(dd, J=7.2, 3.9Hz, 2H), 6.74(s, 1H), 6.65(s, 1H), 4.99(qd,...

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Abstract

The invention discloses an allene thiocyanide derivative and a synthesis method thereof. Propargylamine and trifluoromethylthio silver are used as raw materials, a haloid is used as an additive, an organic solvent is used as a solvent, and a two-step tandem reaction is carried out at room temperature to obtain the allene thiocyanide derivative. The synthesis method of the allene thiocyanide derivative has the advantages of simple operation, safety, high efficiency, mild condition and the like.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine and chemical industry, and in particular relates to a class of allene thiocyanide derivatives and a synthesis method thereof. Background technique [0002] Allene structures exist in natural products and pharmaceuticals. Allenes have many reactive sites and are important intermediates in organic synthesis. Thiocyanide not only shows excellent biological and pharmacological activities, such as antibacterial, anti-proliferation and other activities, but also synthesizes other sulfur-containing compounds such as trifluoromethyl sulfide, thiol, thioether, disulfide, or heterocyclic compounds important precursors. The existing synthesis methods of allene thiocyanides have the disadvantages of requiring highly toxic reagents, step-by-step reactions, cumbersome operations, low safety, high cost, and narrow substrate range. Contents of the invention [0003] The present invention overcomes the shor...

Claims

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Application Information

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IPC IPC(8): C07B45/00C07C331/10C07C331/04C07D317/56
CPCC07B45/00C07C331/04C07C331/10C07D317/56
Inventor 姜丽琴甄龙袁坤张琛云杨俊姚智
Owner EAST CHINA NORMAL UNIVERSITY
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