CN111440198A - 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound and preparation method thereof - Google Patents

1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound and preparation method thereof Download PDF

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CN111440198A
CN111440198A CN202010285459.6A CN202010285459A CN111440198A CN 111440198 A CN111440198 A CN 111440198A CN 202010285459 A CN202010285459 A CN 202010285459A CN 111440198 A CN111440198 A CN 111440198A
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dihydro
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程斌
张昕平
李慧
李运通
汪太民
贺一轩
翟宏斌
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Shenzhen Polytechnic
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Abstract

The invention mainly aims to provide a 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound and a preparation method thereof. The method realizes that the sulfur-containing ylide reacts with allene at 65 ℃ under the condition of taking dichloromethane as a solvent without participation of other reagents, can efficiently synthesize the 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound, and also provides a preparation method of the compound. The invention can simply construct aza-hexatomic ring and heptatomic ring framework without adding other reaction reagents, is expected to be applied to the synthesis work of drug molecules, has easily obtained reaction raw materials, simple reaction operation, no need of adding other noble metal catalysts, convenient post-treatment, wide substrate applicability and generally high yield, and does not need inert gas protection in the preparation process. The reaction condition is mild, the reaction can be rapidly and smoothly carried out at the temperature of 65 ℃, and the mass preparation is easy.

Description

1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound and preparation method thereof
Technical Field
The invention relates to the field of chemical synthesis, in particular to a 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur azepine compound and a preparation method thereof.
Background
nitrogen and sulfur elements are widely present in nature and organisms, nitrogen-containing compounds are representative of natural organic alkaloids, which play An extremely important role in the medical field, sulfur-containing compounds are widely used in materials, pharmaceuticals and even foods, organic sulfur compounds play An important role in organic chemistry because of their excellent properties.therefore, efforts have been made to develop effective methods for introducing sulfur into organic frameworks.seven-membered ring systems frameworks are present in many natural products and pharmaceutical molecular frameworks.e.g. midozolam, alprazolam and triazolam are tricyclic 1, 4-benzodiazepines Fused with imidazole and triazole, which are called psychopharmaceuticals.furthermore, polycyclic 1,4 benzodiazepine and cyclopamine are isolated from aspergillus and penicillium, which exhibit excellent pharmacological activity.a pyridine-sulfur nitrogen complexes are also important cyclic compounds.2015, which are also important polycyclic compounds because of the forces between molecules, which exist in Synthesis of microorganisms, which is a complicated by chemical engineering [ 12. see patent No. 5. see No. 5. fig. 5. 7. see No. 5. 7. experiments.
Disclosure of Invention
One of the purposes of the invention is to provide a 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound, the structural formula of which is shown as a compound I,
Figure BDA0002448347720000021
Wherein R is 1Is H, CH (OMe) 2；R2Benzyl, phenyl and allyl; EWG 1Is methoxycarbonyl, ethoxycarbonyl, benzoyl; EWG 2Methoxycarbonyl, ethoxycarbonyl and benzoyl.
Another object of the present invention is to provide a process for the preparation of 1,10 a-dihydro-2H-pyrido [1,2-d ] [1,4] thiazepine compounds, characterized in that the process is of the formula:
Figure BDA0002448347720000022
The preparation method of the target compound I comprises the following steps:
S1, dissolving a compound II and a compound III in a dichloromethane solvent;
S2, after the compound III disappears completely, removing the organic solvent from the reaction mixture under the reduced pressure condition;
And S3, carrying out silica gel column chromatography elution to obtain a compound I.
In S1, compound II and compound III were used as starting materials, and dichloromethane was used as a solvent, and the temperature was raised to 65 ℃.
The molar ratio of compound II to compound III was 1.2: 1.0, and when the equivalent of compound II increased to 1.5 equivalents, the yield of the corresponding reaction decreased, and the concentration of the dichloromethane solution was 0.1M.
The eluent used for the silica gel column chromatography in the S3 is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio is V Petroleum ether :VEthyl acetate ＝6:1～2:1。
In the S3, the solvent can be replaced by acetonitrile, 1, 2-dichloroethane and ethyl acetate conventional solvents, and the yield is slightly low.
In the S3, the reactant proportion ensures that the product can be obtained when the allenoic acid ester is excessive, and the yield is slightly low.
The invention also provides an application mode, which is as follows: application of 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound in organic chemistry or pharmaceutical chemistry
The invention has the beneficial effects that: the method uses a novel organic sulfur-containing ylide and allene as reactants, and can obtain the 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur-nitrogen compound after the reaction is finished.
The method can easily prepare the 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur and nitrogen compounds, has easily obtained reaction raw materials, simple reaction operation, no need of adding other noble metal catalysts, convenient post-treatment, wide substrate applicability and generally high yield, and does not need inert gas protection in the preparation process. The reaction condition is mild, the reaction can be rapidly and smoothly carried out at the temperature of 65 ℃, and the mass preparation is easy.
Drawings
FIG. 1 is a hydrogen spectrum of compound I-1 (formula E);
FIG. 2 is a hydrogen spectrum of compound I-1 (formula E);
FIG. 3 is a hydrogen spectrum of compound I-1 (formula Z);
FIG. 4 is a carbon spectrum of compound I-1 (formula Z).
Detailed Description
The technical scheme of the invention is further explained by specific embodiments in the following with the accompanying drawings:
Example 1
The reaction formula of example 1, the structures of the compound II-1 and the compound III-1 and the product I-1 are shown in the following formula, and experiments show that the preferred organic solvent of the invention is dichloromethane, the highest yield of the reaction product is 87%, and the best raw material molar ratio is the compound II: when the equivalent amount of compound III was increased to 1.5 equivalents, the yield of the corresponding reaction was decreased and the optimum concentration of the solution was 0.1M, compound III was 1.2: 1.0.
Figure BDA0002448347720000041
the specific experimental procedure was to dissolve 91mg (0.36mmol, 1.2 equiv.) of compound II-1 and 52mg (0.30mmol, 1.0 equiv.) of compound III-1 in 3m L dichloromethane, heat to 65 deg.C for reaction, thin layer chromatography to monitor the disappearance of the reaction III-1, rotary evaporation of the reaction mixture under reduced pressure from a water pump to remove the solvent dichloromethane, 200-300 mesh silica gel as residue, and eluent (volume ratio V) Petroleum ether :VEthyl acetate And (6: 1-2: 1) performing column chromatography to obtain 128 mg (Z: E: 6:1) of the compound shown in I-1, and performing nuclear magnetic (hydrogen spectrum and carbon spectrum) and high-resolution mass spectrum identification on the product.
The product I-1 (formula E) was a yellow oil in 70% yield. 1H NMR(400MHz,(CD3)2CO)7.44–7.31(m,5H),6.44(dd,J＝2.4,1.2Hz,1H),6.00–5.94(m,2H),5.55–5.50(m,1H),5.44–5.38(m,1H),5.37–5.32(m,1H),5.18(s,2H),4.21–4.12(m,1H),3.76(s,3H),3.71(s,3H),2.62(dt,J＝17.2,2.8Hz,1H)；13C NMR(100MHz,(CD3)2CO)165.2(2C),164.6,157.8,145.1,137.1,129.3,129.0,128.9,128.0,125.9,123.8,120.2,108.1,107.6,66.6,57.5,53.4,53.0,36.5；ESI-HRMS m/z calcd for C22H21NO6S[M+H]+428.1162,found 428.1170.
The product I-1 (formula Z) was a yellow oil in 13% yield. 1H NMR(400MHz,(CD3)2CO)7.47–7.30(m,5H),6.20(d,J＝7.6Hz,1H),6.16(s,1H),6.07–6.00(m,1H),5.35–5.26(m,2H),5.20(d,J＝12.4Hz,1H),5.16(d,J＝12.4Hz,1H),4.65(s,1H),3.84(s,3H),3.75(s,3H),3.17(d,J＝14.8Hz,1H),3.01(d,J＝14.4Hz,1H)；13C NMR(100MHz,(CD3)2CO)166.4,166.0,164.8,155.9,147.8,137.4,133.0,129.3,129.2,128.9,126.4,120.5,114.6,112.1,106.2,66.4,62.4,53.5,53.1,40.4；ESI-HRMS m/z calcd for C22H21NO6S[M+H]+428.1162,found428.1169.
the procedure used in the examples for the preparation of the other compounds of the invention (compounds I-2 to I-7) was the same as in example 1, the reaction conditions being that compound II (0.36mmol, 1.2 equiv.) and compound III (0.30mmol, 1.0 equiv.) were dissolved in 3m L dichloromethane and the reaction was allowed to warm to 65 ℃ for reaction, thin layer chromatography was used to monitor the disappearance of the reaction III, the reaction mixture was evaporated under reduced pressure from a water pump to remove the solvent dichloromethane, the residue was applied to 200-300 mesh silica gel and the eluent (volume ratio V) was applied Petroleum ether :VEthyl acetate And (6: 1) carrying out column chromatography to obtain I. II
Example 2
Other related starting materials for the preparation of compounds I-2 through I-7 are the following structures:
Figure BDA0002448347720000061
The chemical structures and data of the compounds I-2 to I-7 of the present invention are characterized:
Figure BDA0002448347720000062
The product I-2 (formula E) was a yellow oil in 63% yield. 1H NMR(400MHz,(CD3)2CO)6.42(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)；13C NMR(100MHz,(CD3)2CO)165.2(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 C18H19NO6S[M+H]+378.1006,found378.1012.
The product I-2 (formula Z) was a yellow oil in 11% yield. 1H NMR(400MHz,(CD3)2CO)6.19(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＝10.4,1.2Hz,1H),4.68–4.60(m,3H),3.84(s,3H),3.76(s,3H),3.18(dd,J＝14.4,4.4Hz,1H),3.04(dd,J＝14.4,3.6Hz,1H)；13C NMR(100MHz,(CD3)2CO)166.4,165.8,164.8,155.7,147.7,133.8,133.1,126.4,120.5,118.2,115.1,112.2,106.0,65.3,62.5,53.4,53.1,40.5；ESI-HRMSm/z calcd for C18H19NO6S[M+H]+378.1006,found378.1013.
The product I-3 (formula E) was a yellow oil in 61% yield. 1H NMR(400MHz,(CD3)2CO)7.42(t,J＝7.8Hz,2H),7.26(t,J＝7.4Hz,1H),7.17(d,J＝8.8Hz,2H),6.60(dd,J＝2.4,0.8Hz,1H),6.02(d,J＝7.6Hz,1H),5.98(dd,J＝9.6,1.6Hz,1H),5.53(dd,J＝9.4,5.4Hz,1H),5.44–5.30(m,2H),4.21–4.11(m,1H),3.79(s,3H),3.74(s,3H),2.73(dt,J＝17.6,2.6Hz,1H)；13CNMR(100MHz,(CD3)2CO)165.2,163.2,160.4,151.5,145.6,130.2,128.2,126.6,124.1,124.0,122.5,120.2,107.7,57.8,53.4,53.0,36.5,(2C missing)；ESI-HRMS m/z calcdfor C21H19NO6S[M+H]+414.1006,found 414.1008.
The product I-3 (formula Z) was a yellow oil in 26% yield. 1H NMR(400MHz,(CD3)2CO)7.43(t,J＝8.0Hz,2H),7.26(t,J＝7.4Hz,1H),7.18(d,J＝8.8Hz,2H),6.38(s,1H),6.23(d,J＝7.6Hz,1H),6.13–6.04(m,1H),5.43–5.32(m,2H),4.69(br s,1H),3.85(s,3H),3.75(s,3H),3.26(dd,J＝14.8,4.4Hz,1H),3.14(dd,J＝14.6,3.8Hz,1H)；13C NMR(100MHz,(CD3)2CO)166.3,164.8,164.5,158.4,151.7,148.4,133.0,130.2,126.4,122.6,120.6,113.7,111.4,106.5,62.7,53.5,53.1,40.6,(1C missing)；ESI-HRMS m/z calcd for C21H19NO6S[M+H]+414.1006,found 414.1009.
The product I-4 (formula E) was a yellow oil in 67% yield. 1H NMR(400MHz,(CD3)2CO)7.50–7.25(m,5H),6.43(d,J＝1.2Hz,1H),6.02–5.94(m,2H),5.51(dd,J＝9.4,5.4Hz,1H),5.41–5.30(m,2H),5.18(s,2H),4.32–4.08(m,5H),2.63(dt,J＝17.2,2.6Hz,1H),1.28(t,J＝7.2Hz,3H),1.24(t,J＝7.2Hz,3H)；13C NMR(100MHz,CD3)2CO)164.7,164.6(2C),158.0,145.1,137.1,129.3,128.9(2C),128.2,125.3,123.9,120.0,108.9,107.3,66.6,62.8,62.3,57.7,36.4,14.3,14.1；ESI-HRMS m/z calcd for C24H25NO6S[M+H]+456.1475,found 456.1480.
The product I-4 (formula Z) was a yellow oil in 16% yield. 1H NMR(400MHz,(CD3)2CO)7.45–7.30(m,5H),6.18(d,J＝8.0Hz,1H),6.17(s,1H),6.05–6.00(m,1H),5.31–5.25(m,2H),5.20(d,J＝12.4Hz,1H),5.16(d,J＝12.4Hz,1H),4.67(br s,1H),4.36–4.16(m,4H),3.17(dd,J＝14.4,4.4Hz,1H),3.01(dd,J＝14.8,3.2Hz,1H),1.31(t,J＝6.8Hz,3H),1.28(t,J＝6.8Hz,3H)；13C NMR(100MHz,(CD3)2CO)166.0,165.9,164.2,156.0,147.2,137.5,133.2,129.3,129.2,128.9,126.4,120.4,116.4,112.1,105.6,66.4,63.0,62.6,62.5,40.5,14.3,14.2；ESI-HRMS m/z calcd for C24H25NO6S[M+H]+456.1475,found 456.1482.
The product I-5 (formula E) was a red oil in 57% yield. 1H NMR(400MHz,(CD3)2CO)7.91–7.87(m,2H),7.80–7.76(m,2H),7.57(t,J＝7.6Hz,1H),7.84(t,J＝7.6Hz,1H),7.47–7.33(m,9H),6.45(dd,J＝2.0,0.8Hz,1H),5.93(dd,J＝9.4,5.4Hz,1H),5.85(d,J＝7.2Hz,1H),5.73–5.67(m,1H),5.61–5.56(m,1H),5.21(s,2H),5.15–5.10(m,1H),4.45–4.32(m,1H),2.90(dt,J＝17.2,2.8Hz,1H)；13C NMR(100MHz,CD3)2CO)192.3,191.8,164.7,157.9,149.5,138.4,137.1(2C),134.3,133.4,130.1,129.8,129.4,129.3,129.0(2C),124.7,124.6,122.3,119.4,106.9,66.7,57.8,37.3,(2C missing)；ESI-HRMS m/z calcd for C32H25NO4S[M+H]+520.1577,found 520.1578.
The product I-5 (Z formula) was a yellow oil in 4% yield. 1H NMR(400MHz,(CD3)2CO)7.90–7.85(m,2H),7.78–7.73(m,2H),7.64–7.57(m,2H),7.54–7.45(m,4H),7.40–7.31(m,5H),6.23(s,1H),6.08(d,J＝7.6Hz,1H),6.06–5.99(m,1H),5.42–5.34(m,1H),5.28–5.20(m,1H),5.13(s,2H),4.78(br s,1H),3.57(dd,J＝14.8,3.6Hz,1H),3.28(dd,J＝14.8,4.0Hz,1H)；13CNMR(100MHz,(CD3)2CO)193.9,193.5,165.9,155.7,153.6,137.5,137.4,137.2,134.5,134.0,133.1,130.1(2C),129.7,129.4,129.3,129.2,128.9,126.4,122.1,120.1,112.6,106.7,66.4,62.7,40.6；ESI-HRMS m/z calcd for C32H25NO4S[M+H]+520.1577,found520.1574.
The product I-6 (formula E) was a yellow oil in 30% yield. 1H NMR(400MHz,(CD3)2CO)7.88(d,J＝7.2Hz,2H),7.64(t,J＝7.4Hz,1H),7.53(t,J＝7.6Hz,2H),7.42–7.33(m,5H),6.34(d,J＝0.8Hz,1H),6.13(d,J＝7.6Hz,1H),5.99(dd,J＝9.4,5.4Hz,1H),5.44(dd,J＝9.6,4.4Hz,1H),5.22–5.17(m,4H),4.37(dd,J＝16.0,7.2Hz,1H),3.43(s,3H),2.86–2.80(m,1H)；13CNMR(100MHz,(CD3)2CO)191.2,164.7,163.9,157.0,139.7,137.2(2C),134.2,132.5,129.9,129.6,129.3,129.0,128.9,125.2,121.6,118.3,104.0,66.6,59.2,52.8,35.6,(1Cmissing)；ESI-HRMS m/z calcd for C27H23NO5S[M+H]+474.1370,found 474.1379.
The product I-6 (Z formula) was a red oil in 14% yield. 1H NMR(400MHz,(CD3)2CO)7.90(d,J＝6.8Hz,2H),7.69(t,J＝7.6Hz,1H),7.58(t,J＝7.6Hz,2H),7.40–7.30(m,5H),6.23(s,1H),6.22(d,J＝7.6Hz,1H),6.05–5.97(m,1H),5.23–5.18(m,1H),5.14(s,2H),5.11–5.06(m,1H),4.90–4.85(m,1H),3.59(s,3H),3.35(dd,J＝14.0,4.8Hz,1H),3.01(dd,J＝14.6,2.2Hz,1H)；13C NMR(100MHz,(CD3)2CO)192.0,165.9,163.9,155.2,141.2,137.2,136.1,135.2,134.6,133.9,130.0,129.8,129.3,129.2,128.9,126.6,119.5,113.4,102.1,66.5,62.0,53.0,41.0；ESI-HRMS m/z calcd for C27H23NO5S[M+H]+474.1370,found 474.1376.
The product I-7 (formula E) was a yellow oil in 62% yield. 1H NMR(400MHz,(CD3)2CO)7.42–7.31(m,5H),6.45(d,J＝1.2Hz,1H),6.01(d,J＝7.2Hz,1H),5.61–5.59(m,1H),5.49–5.43(m,1H),5.37(d,J＝7.6Hz,1H),5.18(s,2H),4.74(s,1H),4.15(dd,J＝17.2,10.0Hz,1H),3.76(s,3H),3.71(s,3H),3.24(s,6H),2.71–2.63(m,1H)；13C NMR(100MHz,(CD3)2CO)165.1,164.6,157.5,151.5,144.7,137.0,133.7,129.3,128.9,128.3,126.0,123.3,117.9,108.6,106.2,102.4,66.6,57.6,53.4,53.0,52.8,52.7,36.5；ESI-HRMS m/z calcd forC25H27NO8S[M+H]+502.1530,found502.1537.
The product I-7 (Z formula) was a yellow oil in 12% yield. 1H NMR(400MHz,(CD3)2CO)7.43–7.33(m,5H),6.23(d,J＝7.6Hz,1H),6.20(s,1H),5.38(s,1H),5.32(dd,J＝7.6,1.6Hz,1H),5.18(s,2H),4.72(br s,2H),3.83(s,3H),3.76(s,3H),3.23–3.16(m,1H),3.20(s,3H),3.19(s,3H),3.07(dd,J＝14.8,3.6Hz,1H)；13C NMR(100MHz,(CD3)2CO)166.4,166.0,164.7,155.8,147.1,137.5,136.2,133.4,129.3,129.1,128.9,118.3,115.9,112.4,104.6,102.5,66.4,62.6,53.5,53.1,52.9,52.6,40.6；ESI-HRMS m/z calcd for C25H27NO8S[M+H]+502.1530,found 502.1539。
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.

Claims (7)

1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] thiazepine compounds characterized by: the structural formula of the 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur nitrogen compound is shown as a compound I in the following formula,
Figure FDA0002448347710000011
Wherein R is 1Is H, CH (OMe) 2；R2Benzyl, phenyl and allyl; EWG 1Is methoxycarbonyl, ethoxycarbonyl, benzoyl; EWG 2Methoxycarbonyl, ethoxycarbonyl and benzoyl.
2. A process for the preparation of a 1,10 a-dihydro-2H-pyrido [1,2-d ] [1,4] azepine of claim 1 of the formula:
Figure FDA0002448347710000012
The preparation method of the compound I comprises the following steps:
S1, dissolving a compound II and a compound III in a dichloromethane solvent;
S2, after the compound III disappears completely, removing the organic solvent from the reaction mixture under the reduced pressure condition;
And S3, carrying out silica gel column chromatography elution to obtain a compound I.
3. A process according to claim 2 for the preparation of the 1,10 a-dihydro-2H-pyrido [1,2-d ] [1,4] thiazepine compound of claim 1, wherein: in S1, compound II and compound III were used as starting materials, and dichloromethane was used as a solvent, and the temperature was raised to 65 ℃.
4. A process according to claim 3 for the preparation of the 1,10 a-dihydro-2H-pyrido [1,2-d ] [1,4] thiazepine compound of claim 1, wherein: the molar ratio of compound II to compound III was 1.0: 1.2, and the concentration of the dichloromethane solution was 0.1M.
5. A process according to claim 2 for the preparation of 1,10 a-dihydro-2H-pyridine [1,2-d ] according to claim 1 ][1,4]The method for preparing the sulfur-nitrogen compound is characterized by comprising the following steps: the eluent used for the silica gel column chromatography in the S3 is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio is V Petroleum ether :VEthyl acetate ＝6:1～2:1。
6. A process according to claim 2 or 3 for the preparation of the 1,10 a-dihydro-2H-pyrido [1,2-d ] [1,4] thiazepine compound of claim 1, wherein: the dichloromethane solvent may be replaced by acetonitrile solvent, 1, 2-dichloroethane solvent or ethyl acetate solvent.
7. A1, 10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur azepine compound composition is characterized by comprising a 1,10 a-dihydro-2H-pyridine [1,2-d ] [1,4] sulfur azepine compound.
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CN114805286A (en) * 2022-05-06 2022-07-29 深圳职业技术学院 Preparation method of naphtho-oxo-thiazepine derivative

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Publication number Priority date Publication date Assignee Title
CN114805286A (en) * 2022-05-06 2022-07-29 深圳职业技术学院 Preparation method of naphtho-oxo-thiazepine derivative
CN114805286B (en) * 2022-05-06 2023-06-16 深圳职业技术学院 Preparation method of naphthoxythiazepine derivative

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