CN109180607B - Method for synthesizing thiazine diketone heterocyclic compound by catalyzing carbonyl sulfide conversion with organic catalyst - Google Patents
Method for synthesizing thiazine diketone heterocyclic compound by catalyzing carbonyl sulfide conversion with organic catalyst Download PDFInfo
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Abstract
The invention provides a method for synthesizing a thiazine diketone heterocyclic compound by catalyzing carbonyl sulfide conversion with an organic catalyst, and belongs to the technical field of organic synthesis, pesticides and pharmaceutical chemical synthesis. Adding a dienamide compound raw material and a solvent into an autoclave, adding azacyclo-carbene, aza-polar olefin or an adduct of the aza-polar olefin and carbonyl sulfide as an organic catalyst, introducing carbonyl sulfide gas, stirring for 12 hours at 60-100 ℃, cooling to room temperature after the reaction is finished, slowly releasing unreacted carbonyl sulfide gas, draining the solvent to obtain a crude product, and purifying by column chromatography to obtain the 1, 3-thiazine-2, 4-diketone compound. The invention uses carbonyl sulfide to replace the traditional sulfur source, and the reaction has the characteristics of cleanness, mild reaction condition, high functional group tolerance, high conversion rate and stereoselectivity, and has wide application in organic synthesis, pesticides and medicines.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, pesticides and pharmaceutical chemical synthesis, and relates to a method for synthesizing a 6-alkylidene-1, 3-thiazine-2, 4-diketone compound by catalyzing and converting carbonyl sulfide and a dienamide compound to perform cyclization reaction by using an organic small molecular catalyst.
Background
Heterocyclic skeletons containing oxygen, nitrogen and sulfur heteroatoms are representative structures in many synthetic drugs, biomolecules and natural products, in particular six-membered heterocyclic thiazinone compounds, which have attracted a great deal of attention as biologically active substances and important intermediates in pharmaceutical and organic synthetic chemistry, for example thiazinanedione (N-methyl-1, 3-thiazine- [6,5-b ] indole-2, 4-dione) is a class of sulfur-containing heterocyclic phytoalexins that effectively inhibit the growth of pathogenic microorganisms. Therefore, the green and efficient construction of thiazine heterocyclic compounds has important theoretical research and practical significance.
According to the previous research reports, the construction of thiazine heterocyclic molecules is basically prepared by using thiocyanic acid, 2-mercapto aromatic acid, thiourea, carbon disulfide, sulfur powder, thioacetamide and the like as sulfur sources. Despite some advances, these reactions are mostly achieved by stoichiometric reactions and suffer from a single type (Shestakov, a.s.; prefent, m.a.; zlatovskaya, e.o.; Shikhaliev, k.s.; falalev, a.v.; sidornko, o.e. chemistry of Heterocyclic Compounds 2015,51,370.), a complex reaction route (Soliman, a.m. phoshor, Sulfur, and Silicon and the Related Elements 1994,97,1.), severe reaction conditions (Youssef, a.m.; Azab, m.e., yuref, m.m.m.modules, 17,6930.), and the like. In addition, the preparation of buprofezin compounds by using metallic nickel to catalyze the reaction of thiourea with o-iodobenzamide was also reported by K.Takagi et al in 1990 (Takagi, K.chemistry Letters 1990,19, 2205.). However, the research of constructing the thiazine heterocyclic compound by using carbonyl sulfide as a sulfur source and catalyzing the carbonyl sulfide by using an organic small molecular catalyst has not been reported so far.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a method for selectively preparing thiazine diketone heterocyclic compounds by catalyzing carbonyl sulfide and bisacrylamide cyclization reaction by using an organic small-molecule catalyst. The reaction raw materials and reagents are simple and easy to obtain, the applicability of the substrate is wide, the post-treatment process is simple, the target product can be obtained with high yield, high chemical selectivity and high stereoselectivity, and the atom economy is realized.
The invention takes carbonyl sulfide and dienamide derivatives as raw materials, and the thiazine diketone six-membered heterocyclic sulfide compound is synthesized by catalytic cyclization reaction under the action of an organic small molecular catalyst.
The technical scheme of the invention is as follows:
a method for synthesizing thiazine diketone heterocyclic compound by catalyzing carbonyl sulfide conversion with organic catalyst comprises the following steps: adding a dienamide compound and a solvent into an autoclave, adding an N-heterocyclic carbene carbonyl sulfide adduct or an N-heterocyclic olefin carbonyl sulfide adduct as an organic catalyst, introducing carbonyl sulfide gas, stirring at 60-100 ℃ for 12 hours, cooling to room temperature after the reaction is finished, slowly releasing unreacted carbonyl sulfide gas, pumping out the solvent to obtain a crude product, and purifying by column chromatography to obtain a 1, 3-thiazine-2, 4-diketone compound; the reaction is shown as follows:
wherein R is1Is phenyl, methyl, ethyl, isopropyl, n-hexyl, cyclopentyl or cyclohexyl;
R2is hydrogen, methyl, ethyl or phenyl;
R3is benzyl, n-butyl, isopropyl, cyclohexyl, allyl or tosylmethyl.
The structural formula of the organic catalyst is as follows:
n-heterocyclic carbene carbonyl sulfide adduct:
azacycloolefm carbonyl sulfide adduct:
wherein R is4And R5Is methyl, isopropyl, tert-butyl, phenyl, 2,4, 6-trimethylphenyl or 2, 6-diisopropylphenyl, R4And R5The same or different;
R6and R7Is hydrogen, methyl, ethyl or isopropyl, R6And R7The same or different;
R8is methyl, ethyl, isopropyl, n-butyl or benzyl; n is 1 or 2;
further, the nitrogen heterocyclic carbene carbonyl sulfide adduct has a structural formula as follows a-f:
the structural formula of the azacyclo-olefin carbonyl sulfide adduct is as follows g-j:
the molar ratio of the organic catalyst to the bisacrylamide compound is 1: 20.
The solvent is dichloromethane, tetrahydrofuran, toluene, N-dimethylformamide, dimethyl sulfoxide, 1, 4-dioxane or acetonitrile.
The reaction pressure is 0.1-1.0 MPa, and the high-pressure kettle is an intermittent high-pressure reaction kettle or a continuous high-pressure reaction kettle.
The eluent of the column chromatography is a mixed solvent of n-hexane and ethyl acetate, and the volume ratio of the n-hexane to the ethyl acetate is 5: 1.
The invention has the beneficial effects that: the method adopts the organic micromolecular catalyst to catalyze the cyclization reaction of the carbonyl sulfide and the dienamide derivative, and has the characteristics of mild reaction conditions, safe and simple experimental operation, low toxicity of reaction substrates, environmental friendliness and the like. The reaction raw materials and reagents are simple and easy to obtain, the substrate applicability is wide, the post-treatment process is simple, the target product can be obtained with high yield, high chemical selectivity and high stereoselectivity, the atom economy is realized, and the method has potential application prospects in chemical production of thiazine ketone series pesticides, medicines and the like.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the method of carrying out the present invention and the substrate to which the present invention is applied are not limited thereto.
Example 1
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-benzyl-4-methylpenta-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release the unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 96%.
The structural characterization data of the resulting product are shown below:
1H NMR(500MHz,CDCl3)δ7.44(d,J＝7.0Hz,2H),7.28(dt,J＝16.6,4.7Hz,3H),6.37(s,1H),5.18(s,2H),2.79–2.56(m,1H),1.24(d,J＝6.9Hz,6H).13C NMR(126MHz,CDCl3)δ165.2,164.0,160.0,136.3,129.3,128.6,127.9,113.4,44.7,35.4,21.8.HRMS(ESI):calcd for C14H15NO2S:262.0896[M+H]+.Found:262.0897[M+H]+.IR vC＝O:1689,1651cm-1(vs).
example 2
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-benzyl-4-methylhexane-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 99%.
The structural characterization data of the resulting product are shown below:
1H NMR(400MHz,CDCl3)δ7.51–7.39(m,2H),7.28(dq,J＝14.2,7.0Hz,3H),6.35(s,1H),5.17(s,2H),2.54–2.37(m,1H),1.67–1.46(m,2H),1.21(d,J＝6.9Hz,3H),0.91(t,J＝7.4Hz,3H).13C NMR(101MHz,CDCl3)δ165.2,163.8,159.0,136.2,129.3,128.5,127.9,114.2,44.7,42.8,28.9,19.7,11.7.HRMS(ESI):calcd for C15H17NO2S:276.1053[M+H]+.Found:276.1051[M+H]+.IR vC＝O:1684,1652cm-1(vs).
example 3
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-benzyl-3-cyclohexylidenediamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, the heating and stirring were stopped, the mixture was cooled to room temperature, and unreacted carbonyl sulfide was slowly released. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 87%.
The structural characterization data of the resulting product are shown below:
1H NMR(400MHz,CDCl3)δ7.50(d,J＝6.8Hz,2H),7.41–7.26(m,3H),6.41(s,1H),5.23(s,2H),2.37(m,J＝11.0Hz,1H),1.91(m,J＝17.7,9.9Hz,4H),1.77(d,J＝12.6Hz,1H),1.49–1.17(m,5H).13C NMR(101MHz,CDCl3)δ165.2,163.9,158.9,136.2,129.2,128.4,127.8,113.4,44.9,44.5,32.1,25.9,25.4.HRMS(ESI):calcd for C17H19NO2S:302.1209[M+H]+.Found:302.1211[M+H]+.IR vC＝O:1683,1651cm-1(vs).
example 4
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-benzyl-4, 5-dimethylhex-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, heating and stirring were stopped, and cooling was carried out to room temperature to slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 93%.
The structural characterization data of the resulting product are shown below:
1H NMR(400MHz,CDCl3)δ7.36(d,J＝7.0Hz,2H),7.29–7.09(m,3H),6.25(s,1H),5.08(s,2H),2.30–2.04(m,1H),1.73–1.57(m,1H),1.09(d,J＝7.0Hz,3H),0.84(t,J＝6.6Hz,6H).13C NMR(101MHz,CDCl3)δ165.1,163.7,158.8,136.2,129.2,128.4,127.8,114.5,48.1,44.6,32.6,21.1,19.5,17.0.HRMS(ESI):calcd for C12H15NO2S:290.1209[M+H]+.Found:290.1207[M+H]+.IR vC＝O:1686,1647cm-1(vs).
example 5
A20 ml autoclave was charged with a stirrer, 0.5 mmol of 4-ethyl-N- (prop-2-yn-1-yl) hex-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, stirred at 60 ℃ for 12 hours, then the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release the unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 97%.
The structural characterization data of the resulting product are shown below:
1H NMR(400MHz,CDCl3)δ6.39(s,1H),4.76(d,J＝2.3Hz,2H),2.40–2.14(m,2H),1.73–1.61(m,2H),1.55(tt,J＝14.5,7.4Hz,2H),0.93(t,J＝7.4Hz,6H).13C NMR(101MHz,CDCl3)δ164.3,162.4,157.9,115.0,77.5,71.1,51.0,30.5,27.2,27.0,11.7.HRMS(ESI):calcd for C12H15NO2S:238.0896[M+H]+.Found:235.0895[M+H]+.IR vC＝O:1695,1651cm-1(vs).
example 6
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-benzyl-4-phenylpentane-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, heating and stirring were stopped, and cooling was carried out to room temperature to slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 98%.
The structural characterization data of the resulting product are shown below:
1H NMR(400MHz,CDCl3)δ7.42(d,J＝7.1Hz,2H),7.35–7.13(m,8H),6.43(s,1H),5.12(s,2H),3.79(q,J＝7.0Hz,1H),1.55(d,J＝7.2Hz,3H).13C NMR(101MHz,CDCl3)δ164.8,163.7,157.6,140.2,136.1,129.2,129.0,128.4,127.9,127.8,127.5,114.4,45.5,44.6,19.6.HRMS(ESI):calcd for C19H25NO2S:332.1679[M+H]+.Found:332.1680[M+H]+.IR vC＝O:1682,1651cm-1(vs).
example 7
A20 ml autoclave was charged with a stirrer, 0.5 mmol of 4-phenyl N- (tosylmethyl) penta-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 98%.
The structural characterization data of the resulting product are shown below:
1H NMR(500MHz,CDCl3)δ7.77(d,J＝8.3Hz,2H),7.37(t,J＝7.3Hz,2H),7.32(dd,J＝7.5,3.8Hz,3H),7.24–7.20(m,2H),6.45(s,2H),5.42(s,1H),3.87(q,J＝7.0Hz,3H),2.44(s,2H),1.63(d,J＝7.1Hz,3H).13C NMR(126MHz,CDCl3)δ164.1,162.2,158.8,145.5,139.9,136.2,130.0,129.3,128.7,128.3,127.6,113.9,60.4,45.8,21.8,19.8.HRMS(ESI):calcd for C20H19NO4S2:402.0828[M+H]+.Found:402.0847[M+H]+.IR vC＝O:1698,1658cm-1(vs).
example 8
A20 ml autoclave was charged with a stirrer, 0.5 mmol of 4-phenyl-N- (tosylmethyl) but-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of acetonitrile, and after stirring at 60 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 98%.
The structural characterization data of the resulting product are shown below:
1H NMR(500MHz,CDCl3)δ7.77(d,J＝8.3Hz,2H),7.44–7.28(m,5H),7.24–7.14(m,2H),6.34(s,1H),5.43(s,2H),3.78(s,2H),2.44(s,3H).13C NMR(126MHz,CDCl3)δ164.0,161.9,153.7,145.5,136.3,134.0,130.0,129.3,129.3,128.7,128.3,115.4,60.4,42.2,21.9.HRMS(ESI):calcd for C19H17NO4S2:388.0672[M+H]+.Found:388.0667[M+H]+.IR vC＝O:1698,1656cm-1(vs).
example 9
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-butyl-4-methylpent-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of dimethyl sulfoxide, and after stirring at 100 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release the unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 94%.
The structural characterization data of the resulting product are shown below:
1H NMR(500MHz,CDCl3)δ6.35(s,1H),4.07–3.85(m,2H),2.78–2.62(m,1H),1.59(dt,J＝15.3,7.6Hz,2H),1.36(dq,J＝14.8,7.4Hz,2H),1.26(d,J＝6.9Hz,6H),0.94(t,J＝7.4Hz,3H).13C NMR(126MHz,CDCl3)δ165.0,164.1,159.7,113.3,41.8,35.4,29.8,29.8,21.8,20.3,13.8.HRMS(ESI):calcd for C11H17NO2S:228.1053[M+H]+.Found:228.1051[M+H]+.IR vC＝O:1689,1655cm-1(vs).
example 10
A20 ml autoclave was charged with a stirrer, 0.5 mmol of N-cyclohexyl-4-methylpenta-2, 3-dienamide, 0.025 mmol of THPE-COS (j), and 1 ml of dimethyl sulfoxide, and after stirring at 100 ℃ for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature to slowly release the unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round bottom single neck flask, the reaction kettle was flushed with (3 × 2 ml) dichloromethane, and the solvent was removed in vacuo to give the crude product. The crude product is separated and purified by column chromatography (developing solvent: petroleum ether/ethyl acetate 5: 1). The yield was 98%.
1H NMR(400MHz,CDCl3)δ6.30(s,1H),4.85(tt,J＝12.2,3.7Hz,1H),2.67(hept,J＝6.8Hz,1H),2.33(qd,J＝12.3,3.3Hz,2H),1.87–1.78(m,2H),1.63(dd,J＝7.7,3.6Hz,3H),1.45–1.27(m,3H),1.25(d,J＝6.9Hz,6H).13C NMR(101MHz,CDCl3)δ165.1,164.8,159.6,113.6,55.7,35.1,28.7,26.4,25.3,21.6.HRMS(ESI):calcd for C13H19NO2S:254.1209[M+H]+.Found:254.1213[M+H]+.IR vC＝O:1687,1651cm-1(vs).
Claims (4)
1. A method for synthesizing thiazine diketone heterocyclic compound by catalyzing carbonyl sulfide conversion with organic catalyst is characterized by comprising the following steps: adding a dienamide compound and a solvent into an autoclave, adding an azacycloolefinic carbonyl sulfide adduct as an organic catalyst, introducing carbonyl sulfide gas, stirring for 12 hours at 60-100 ℃, cooling to room temperature after the reaction is finished, slowly releasing unreacted carbonyl sulfide gas, draining the solvent to obtain a crude product, and purifying by column chromatography to obtain a 1, 3-thiazine-2, 4-diketone compound; the reaction is shown as follows:
wherein R is1Is phenyl, methyl, ethyl, isopropyl, n-hexyl, cyclopentyl or cyclohexyl;
R2is hydrogen, methyl, ethyl or phenyl;
R3is benzyl, n-butyl, isopropyl, cyclohexyl, allyl or tosylmethyl;
the structural formula of the azacyclo olefin carbonyl sulfur adduct is as follows i-j:
the solvent is dichloromethane, tetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide, 1, 4-dioxane or acetonitrile.
2. The process of claim 1, wherein the molar ratio of the organic catalyst to the bisacrylamide compound is 1: 20.
3. The method according to claim 1, wherein the reaction pressure is 0.1-1.0 MPa, and the autoclave is a batch high-pressure reactor or a continuous high-pressure reactor; the eluent of the column chromatography is a mixed solvent of n-hexane and ethyl acetate, and the volume ratio of the n-hexane to the ethyl acetate is 5: 1.
4. The method according to claim 2, wherein the reaction pressure is 0.1-1.0 MPa, and the autoclave is a batch high-pressure reactor or a continuous high-pressure reactor; the eluent of the column chromatography is a mixed solvent of n-hexane and ethyl acetate, and the volume ratio of the n-hexane to the ethyl acetate is 5: 1.
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| Fast CO2 Sequestration, Activation, and Catalytic Transformation Using N‑Heterocyclic Olefins;Yan-Bo Wang et al.;《J. Am. Chem. Soc.》;20130718;第135卷;第11996-12003页 * |
| Ultrasound-mediated three-component reaction "on-water" protocol for the synthesis of novel mono- and bis-1,3-thiazin-4-one derivatives;Wael A.A.Arafa et al.;《Heterocycles》;20170609;第94卷(第8期);第1439-1455页 * |
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