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Synthesis method of conjugated alkenyl amidine compound

A synthesis method and compound technology, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of poor universality of substrates, and achieve the effects of easy separation and purification, stable products, and reduced environmental pollution

Active Publication Date: 2021-07-20
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, the substrate universality of this method is not good, and only two cases of conjugated alkenyl amidine products were obtained.

Method used

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  • Synthesis method of conjugated alkenyl amidine compound
  • Synthesis method of conjugated alkenyl amidine compound
  • Synthesis method of conjugated alkenyl amidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～24

[0061] The following examples 1 to 24 were all reacted under optimal reaction conditions. The specific reaction equation is as follows, mainly to investigate the yield of different substrates under optimal conditions:

[0062] Concrete reaction formula is as follows:

[0063]

[0064] The specific operation steps are:

[0065] Potassium fluoride (0.046g, 4.0equiv) and 18-crown-6 (0.052g, 1.0equiv) were sequentially added into a clean and dry Schlenk tube, the double exhaust tube was evacuated and replaced with nitrogen for three times, and the The isonitrile compound (1.0 equiv), Kobayashi aryne precursor derivative (1.5 equiv) and DMF (1.0 mL) were added at the same time. The mixture was stirred at room temperature for 5 h, and a sample was taken for detection. TLC monitored that the reaction raw materials disappeared completely. Add 1M H to the reaction system 2 O was diluted and extracted three times with ethyl acetate, the organic phases were combined, washed with sa...

Embodiment 1

[0067] Compound 1: The yield is 85%.

[0068]

[0069] 1 H NMR (400MHz, CDCl 3 -d) δ7.91(s,1H),7.21(ddd,J=8.5,7.2,1.7Hz,1H),7.14(dd,J=7.8,1.7Hz,1H),7.08(s,1H),6.91 (dd, J=8.2,1.3Hz,1H),6.80(td,J=7.4,1.3Hz,1H),4.29(q,J=7.1Hz,2H),3.08(s,3H),3.05(s, 3H), 1.37(t, J=7.1Hz, 3H); 13 CNMR (100MHz, CDCl 3 -d) δ165.4, 158.5, 154.9, 132.4, 130.6, 125.9, 125.5, 123.8, 123.4, 119.0, 61.7, 41.5, 35.2, 14.4; HRMS(ESI) m / z calcd for C 14 h 18 N 2 o 3 + [M+H] + 263.1390,found263.1390.

Embodiment 2

[0071] Compound 2: The yield is 72%.

[0072]

[0073] 1 H NMR (400MHz, CDCl 3-d) δ7.88(s,1H),7.09(s,1H),6.99(s,1H),6.79(s,1H),4.28(q,J=7.1Hz,2H),3.04(d,J =13.9Hz, 6H), 2.83(dt, J=21.6, 7.4Hz, 4H), 2.04(p, J=7.4Hz, 2H), 1.36(t, J=7.2Hz, 3H); 13 C NMR (100MHz, CDCl3-d) δ166.0, 156.2, 154.6, 148.0, 134.8, 130.3, 127.9, 127.8, 120.7, 114.8, 61.26, 41.3, 35.1, 33.2, 31.8, 26.0, 14.5; HRMS (ESI) m / z calcd for C 17 h 22 N 2 o 3 + [M+H] + 303.1703,found 303.1706.

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Abstract

The invention discloses a synthetic method of a conjugated alkenyl amidine compound, which comprises the following step: carrying out one-pot reaction on a Kobayashi aryne precursor derivative, N,N-dimethylformamide and an isonitrile compound under the action of fluorine ions to obtain the conjugated alkenyl amidine compound. According to the method, transition metal or noble metal catalysts are not needed, the reaction conditions are mild, the steps are simple, the substrate universality is good, the yield is good, and an intermediate raw material source is provided for drug synthesis.

Description

technical field [0001] The present invention relates to a synthetic method of conjugated alkenyl amidines, in particular to a three-component Kobayashi aryne precursor derivative, N,N-dimethylformamide and isonitrile compound under the catalysis of fluoride ions in a mild The invention provides a one-pot reaction under reaction conditions to obtain conjugated alkenyl amidine derivatives with stable structure and easy separation, and belongs to the technical field of pharmaceutical intermediate synthesis. Background technique [0002] Azebutadiene can directly and efficiently construct nitrogen-containing heterocycles through the Hetero-Diels-Alder strategy. It has been proved to be a practical construction skeleton in organic synthesis, and is widely used in chiral piperidine, quinoline, pyridazine, and oxazine. And the synthesis of oxadiazine derivatives and fused ring compounds with higher molecular complexity with these pharmacologically relevant heterocyclic skeletons, t...

Claims

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Application Information

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IPC IPC(8): C07C257/12C07D317/64C07C315/04C07C317/28
CPCC07C257/12C07D317/64C07C315/04C07B2200/13C07C2601/14C07C2602/08C07C317/28Y02E10/549
Inventor 严楠刘瑶王瑞奇王会翔张文峰胡祥国
Owner JIANGXI NORMAL UNIV
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