CN115572300A - Synthesis method of sulfonamide substituted polycyclic quinazolinone compound - Google Patents
Synthesis method of sulfonamide substituted polycyclic quinazolinone compound Download PDFInfo
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Abstract
The invention discloses a synthetic method of a sulfonamide-substituted polycyclic quinazolinone compound, and relates to the fields of medicines, organic chemical industry and fine chemical industry. Under the induction of visible light, N-sulfamide pyridine salt is used as a sulfamide free radical precursor, a sulfamide free radical is generated under the catalysis of a photosensitizer 4CZIPN, and a series of series reaction processes of free radical addition, cyclization reaction, 1, 2-hydrogen migration, single electron transfer, dehydrooxidation and the like are carried out on an N-alkyl quinazolinone compound containing an unactivated double bond, so that the sulfamide substituted polycyclic quinazolinone compound is obtained. The synthetic raw materials are easy to obtain, the reaction is carried out at normal temperature, the post-treatment is convenient, the product yield is high, and the method has a wide application prospect.
Description
Technical Field
The invention belongs to the fields of medicine, organic chemical industry and fine chemical industry, and particularly relates to a synthesis method of a sulfonamide substituted polycyclic quinazolinone compound.
Background
The polycyclic quinazolinone structure widely exists in natural products, alkaloids and other molecules with physiological activity, has various biological activities of resisting cancer, resisting virus, resisting tuberculosis and the like, has good fluorescence property, and is an important nitrogen heterocyclic compound. Pyrroloquinazolines (e.g., desoxyvasicine (Deoxovasicine), luotonin, peharmaline A) and piperidinoquinazolines (Mackinazolinone, leucomodine C) are two important classes of polycyclic quinazolinone compounds, deoxovasicine and Vasicinone being useful in the treatment of cold, cough, bronchitis and asthma. Mackinazolinone and Leucomidine C have antidepressant, antibacterial, anti-inflammatory and anti-cytotoxic properties. Therefore, the intensive research on the synthesis and derivatization reaction of the compound containing the pyrroloquinazolinone or piperidinoquinazolinone structure has important practical application value.
Sulfonamide compounds are a very important compound in pharmaceutical chemistry. Sulfonamide compounds have various pharmacological activities such as antibacterial, antiviral, anticancer, antidepressant, carbonic anhydrase inhibition, and the like, and thus more and more researchers are attracting to make efforts on the structure optimization and the pharmacological effect research of sulfonamide compounds. The sulfonamide group is added into polycyclic quinazolinone as a substituent group, so that the effects of the two compounds are expected to be exerted synergistically, the activity is further improved, and the cytotoxicity is reduced. However, in the existing polycyclic quinazolinone synthesis derivation, the main structural transformation site is located on the benzene ring of the quinazolinone parent nucleus, and the derivation on the fused ring is very little.
Regarding the synthesis of two types of compounds, in the prior art, polycyclic quinazolinones are constructed by a plurality of methods, for example, under the action of silver catalysis, N-cyanamide olefin and diphenylphosphine oxide are taken as radical precursors to carry out phosphorylation/cyclization and other radical series reactions to synthesize 4-quinazolinone and dihydroisoquinolinone (org.Lett.2016, 18, 1768); taking aliphatic aldehyde as an alkyl radical precursor without metal participation, and carrying out free radical addition and cyclization reaction with N-cyanamide olefin to construct a fused ring quinolinone structure (org.chem.Front.2017, 4, 2370.); photocatalytic oxidation/reductive cyclization of N-cyanamidefins with arylsulfinic acids or arylsulfonyl chlorides to give sulfonated fused quinazolinones (org. Lett.2017,19, 4798.); photoinduced free radical tandem trifluoromethylation/N-cyanamide alkene cyclization reaction to synthesize trifluoromethylated fused-ring quinazolinone (J.Org.chem., 2022,87, 1493.). Although the synthesis methods of polycyclic quinazolinone are numerous, the synthesis methods of sulfonamide-substituted quinazolinone derivatives are relatively few, and for sulfonamide-type compounds, the compounds are generally directly synthesized by using sulfonyl chloride and amine, but it is worth noting that the methods are not applicable to the construction of complex sulfonamide-substituted cyclic compounds.
Chinese patent CN 114108013A discloses an electrochemical synthesis method of trifluoromethyl-substituted polycyclic quinazolinone derivatives, which adopts an electrocatalytic oxidative dehydrogenation mode to obtain trifluoromethyl-substituted polycyclic quinazolinone derivatives extending on a parallel ring, and although the method has the advantages of simple operation, high efficiency, cleanness and the like, the problems of high one-time investment, high energy consumption, low space-time efficiency of a reactor and the like existing in the electrochemical method are not ignored, and meanwhile, the electrochemical method has higher requirements on electrode materials, electrolytic cell structures and diaphragm materials when the compound is synthesized, and the defects are still obvious. In addition, the prior art does not show a precedent for successfully applying an electrochemical synthesis technology to synthesis of sulfonamide-substituted polycyclic quinazolinone compounds, the synthesis conditions need to be further researched, the difficulty is high, and the practicability is unpredictable. Therefore, the aim at the present stage is to explore a method for synthesizing the sulfonamide-substituted polycyclic quinazolinone compound, which is environment-friendly, simple and efficient, provide a more reliable way for the synthesis and application of the compound, widen the application prospect of the compound, and provide assistance for the future clinical application of the compound.
Disclosure of Invention
The invention aims to provide a novel and efficient method for synthesizing sulfonamide-substituted polycyclic quinazolinone compounds, so as to obtain a series of molecules with potential physiological activity and provide a basis for the practical application of the compounds.
The technical scheme of the invention is as follows: a synthetic method of sulfonamide substituted polycyclic quinazolinone compounds comprises the following steps: taking N-alkyl quinazolinone containing non-activated double bonds as a substrate, under the catalytic action of a photosensitizer, taking N-sulfonamido pyridine salt as a sulfonamide radical precursor, and synthesizing a sulfonamide-substituted polycyclic quinazolinone new compound in a solvent by using quinazolinone through reaction processes including radical addition, cyclization reaction, 1, 2-hydrogen migration, single electron transfer and dehydroxylation;
the general reaction formula is as follows:
wherein n =1,2;
r is selected from any one of hydrogen, C1-C4 linear alkane, halogen, C1-C4 linear alkoxy and trifluoromethyl, and the position of a substituent can be 5,6, 7 and 8 positions of the quinazolinone mother nucleus;
ar is selected from any one of phenyl, thienyl, p-halophenyl and p-tert-butylphenyl.
Further, the photosensitizer used was 2,4,5, 6-tetrakis (9-carbazolyl) -isophthalonitrile (4 CzIPN).
Furthermore, the synthesis reaction is carried out at room temperature, and the reaction time is 6-12 h.
Further, the concentration of the reactant N-alkyl quinazolinone is 0.05-0.1mmol/mL.
Further, the mass ratio of the N-alkyl quinazolinone and the N-sulfonamidopyridine salt is 1.0 to 2.0.
Further, the light source is a blue light LED lamp strip or a white light LED bulb.
Further, the solvent used is dichloroethane.
Further, the photosensitizer is used in an amount of 2mol%.
Further, after the reaction is finished, the product is obtained by processing through a column chromatography separation method, and an eluent is a mixed solvent of petroleum ether and ethyl acetate.
Compared with the prior art, the invention has the following advantages:
1. the synthesis method of the sulfonamide-substituted polycyclic quinazolinone compound is realized by taking N-sulfonamide pyridine salt as a sulfonamide radical precursor under the induction of visible light, performing free radical addition, cyclization reaction, 1, 2-hydrogen migration, single electron transfer, dehydrooxidation and other series reaction processes on the N-alkyl quinazolinone compound containing an unactivated double bond, and obtaining a series of compound molecules with potential physiological activity by the method;
2. the sulfonamide-substituted polycyclic quinazolinone compound synthesized by the method disclosed by the application is further optimized in structure of sulfonamide compounds, provides richer templates for drug effect research of polycyclic quinazolinone and sulfonamide compounds, provides an effective basis for application research of combined drugs with synergistic effects, has a higher implementation value, and is expected to bring remarkable social and economic benefits;
3. the synthesis method disclosed by the application has the advantages of easily available raw materials, simple synthesis conditions, convenience in post-treatment, high product yield, high overall synthesis efficiency and wide application prospect, and the reaction is carried out at normal temperature.
4. The compound synthesized by the method disclosed by the application has a quinazolinone structure and a sulfonamide group in molecules, so that the synthesis method also provides a reliable way for the new compound of the sulfonamide-substituted polycyclic quinazolinone compound.
Detailed Description
The technical solutions of the present invention are further described below, but not limited thereto, and all modifications or equivalent substitutions made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention should be included in the protection scope of the present invention.
The specific route and the structural formula of the main product of the synthetic method disclosed by the invention are as follows:
example 1
N-but-3-enyl-quinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, evacuated with nitrogen and sealed, and stirred under blue light 6W LED lamp irradiation at room temperature for 12 hours. And (3) after the reaction is finished, removing the solvent under reduced pressure, and performing column chromatography separation to obtain a target product 3aa with the yield of 81%.
1 H NMR(400MHz,CDCl 3 )δ8.19(d,J＝7.9Hz,1H),7.76-7.68(m,3H),7.58 (d,J＝8.0Hz,1H),7.42(t,J＝7.4Hz,1H),7.25(d,J＝7.9Hz,2H),6.49-6.47(m, 1H),4.28-4.23(m,1H),3.95-3.88(m,1H),3.52-3.36(m,2H),3.21-3.15(m,1H), 2.42-2.36(m,1H),2.38(s,3H),2.06-1.94(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ 160.5,159.8,148.4,143.6,136.8,134.3,129.8,126.9,126.8,126.7,126.4,120.7, 44.9,44.6,42.8,23.8,21.5；HRMS(ESI)m/z calcd for C 19 H 20 N 3 O 3 S[M+H + ]: 370.1220,found 370.1220.
Example 2
N-but-3-enyl-8-fluoroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 8 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ba is obtained by column chromatography, wherein the yield is 76%.
1 H NMR(400MHz,CDCl 3 )δ7.84(d,J＝7.6Hz,1H),7.71(d,J＝8.2Hz,2H), 7.35-7.26(m,2H),7.22(d,J＝8.1Hz,2H),6.49-6.46(m,1H),4.25-4.18(m,1H), 3.97-3.90(m,1H),3.52-3.40(m,2H),3.24-3.18(m,1H),2.45-2.39(m,1H),2.35(s, 3H),2.13-2.03(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.5,159.6(d,J C-F ＝3.0 Hz),156.5(d,J C-F ＝253.5Hz),143.5,137.8(d,J C-F ＝11.9Hz),136.7,129.7,126.9, 126.5(d,J C-F ＝7.5Hz),122.5,121.7(d,J C-F ＝4.2Hz),119.6(d,J C-F ＝18.8Hz), 45.3,44.6,43.2,23.7,21.5；HRMS(ESI)m/z calcd for C 19 H 19 FN 3 O 3 S[M+H + ]: 388.1126,found 388.1128.
Example 3
N-but-3-enyl-8-chloroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (3 mL) were added to a Schlenk reaction tube, nitrogen was evacuated and sealed, and stirred at room temperature for 10 hours under the irradiation of a blue 6W LED lamp. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ca is obtained by column chromatography separation, wherein the yield is 70%.
1 H NMR(400MHz,CDCl 3 )δ8.12(d,J＝7.8Hz,1H),7.82-7.78(m,3H),7.35 (t,J＝7.8Hz,1H),7.28(d,J＝8.1Hz,2H),6.93(d,J＝8.5Hz 1H),4.32-4.27(m, 1H),3.98-3.91(m,1H),3.61-3.49(m,2H),3.11-3.06(m,1H),2.46-2.34(m,1H), 2.39(s,3H),1.99-1.88(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.1,159.9,144.9, 143.5,136.6,134.5,131.3,129.8,127.1,126.7,125.2,122.3,45.3,44.9,42.4,24.0, 21.5；HRMS(ESI)m/z calcd for C 19 H 19 ClN 3 O 3 S[M+H + ]:404.0830,found 404.0825.
Example 4
N-but-3-enyl-7, 8-dimethylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to the Schlenk reaction tube, nitrogen was evacuated and sealed, and stirred at room temperature for 12 hours under illumination of a white light 10 watt LED bulb. After the reaction was completed, the solvent was removed under reduced pressure, and column chromatography was performed to obtain the objective product 3da in a yield of 68%.
1 H NMR(400MHz,CDCl 3 )δ7.96(d,J＝8.1Hz,1H),7.77(d,J＝8.3Hz,2H), 7.28(d,J＝8.4Hz,2H),7.23(d,J＝8.2Hz,1H),6.91-6.88(m,1H),4.29-4.23(m, 1H),3.93-3.86(m,1H),3.58-3.51(m,1H),3.46-3.37(m,1H),3.15-3.09(m,1H), 2.47(s,3H),2.42-2.36(m,7H),1.95-1.84(m,1H)； 13 C NMR(101MHz,CDCl 3 ) δ160.9,158.7,146.7,143.5,143.3,136.8,132.9,129.8,128.6,126.9,123.2,118.5, 45.0,44.8,42.2,24.1,21.5,21.0,13.4；HRMS(ESI)m/z calcd for C 21 H 24 N 3 O 3 S [M+H+]:398.1533,found 398.1534.
Example 5
N-but-3-enyl-6, 8-dimethylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.2 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, nitrogen was evacuated and sealed, and stirred at room temperature for 12 hours under the irradiation of a blue 6W LED lamp. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ea is obtained by column chromatography separation, wherein the yield is 75%.
1 H NMR(300MHz,CDCl 3 )δ7.75-7.71(m,3H),7.32(s,1H),7.24(d,J＝8.1 Hz,2H),6.99-6.94(m,1H),4.25-4.17(m,1H),3.92-3.82(m,1H),3.54-3.32(m,2H), 3.13-3.05(m,1H),2.46(s,3H),2.42-2.25(m,7H),1.94-1.80(m,1H)； 13 C NMR(75 MHz,CDCl 3 )δ160.8,158.1,144.8,143.5,136.8,136.4,136.2,134.6,129.8,126.9, 123.4,120.3,45.1,44.9,42.0,24.1,21.5,21.2,17.5；HRMS(ESI)m/z calcd for C 21 H 24 N 3 O 3 S[M+H + ]:398.1533,found 398.1534.
Example 6
N-but-3-enyl-6-chloro-8-methylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.24 mmol), 4CzIPN (2 mol%), dichloroethane (2 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under irradiation of a blue light 6W LED lamp strip. After the reaction, the solvent was removed under reduced pressure, and the desired product, 3fa, was obtained by column chromatography in 67% yield.
1 H NMR(300MHz,CDCl 3 )δ7.88-7.87(m,1H),7.72(d,J＝8.3Hz,2H), 7.43-7.42(m,1H),7.25(d,J＝8.0Hz,2H),6.69-6.65(m,1H),4.27-4.19(m,1H), 3.95-3.85(m,1H),3.56-3.35(m,2H),3.19-3.12(m,1H),2.50-2.34(m,7H), 2.02-1.88(m,1H)； 13 C NMR(75MHz,CDCl 3 )δ159.7,159.2,145.6,143.6,137.4, 136.7,134.8,131.7,129.8,126.9,123.4,121.6,45.1,44.8,42.5,23.9,21.5,17.5； HRMS(ESI)m/z calcd for C 20 H 21 ClN 3 O 3 S[M+H + ]:418.0987,found 418.0991.
Example 7
N-but-3-enyl-7-fluoroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.28 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ga is obtained by column chromatography separation, wherein the yield is 74 percent.
1 H NMR(400MHz,CDCl 3 )δ8.18-8.14(m,1H),7.74(d,J＝8.2Hz,2H),7.27 (d,J＝8.0Hz,2H),7.22-7.18(m,1H),7.14-7.09(m,1H),6.39-6.36(m,1H), 4.28-4.21(m,1H),3.95-3.88(m,1H),3.50-3.39(m,2H),3.26-3.20(m,1H), 2.45-2.37(m,1H),2.38(s,3H),2.10-1.99(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ 166.8(d,J C-F ＝52.7Hz),161.2,159.8,150.7(d,J C-F ＝12.8Hz),143.6,136.8,129.8, 129.0(d,J C-F ＝10.5Hz),126.9,117.4(d,J C-F ＝1.6Hz),115.3(d,J C-F ＝23.4Hz), 112.2(d,J C-F ＝22.0Hz),45.0,44.4,43.1,23.8,21.5；HRMS(ESI)m/z calcd for C 19 H 19 FN 3 O 3 S[M+H + ]:388.1126,found 388.1128.
Example 8
N-but-3-enyl-7-bromoquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred under blue light 6W LED lamp strip irradiation at room temperature for 12 hours. And (3) after the reaction is finished, removing the solvent under reduced pressure, and performing column chromatography separation to obtain a target product 3ha with the yield of 71%.
1 H NMR(400MHz,CDCl 3 )δ8.00(d,J＝8.5Hz,1H),7.76-7.74(m,3H),7.50 (dd,J＝8.5,1.9Hz,1H),7.28(d,J＝8.0Hz,2H),6.35-6.32(m,1H),4.28-4.22(m, 1H),3.95-3.87(m,1H),3.52-3.37(m,2H),3.25-3.19(m,1H),2.45-2.37(m,1H), 2.41(s,3H),2.09-1.99(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.1,160.0,149.5, 143.7,136.8,129.9,129.8,129.6,128.9,127.8,126.9,119.6,45.1,44.3,43.1,23.8, 21.6；HRMS(ESI)m/z calcd for C 19 H 19 BrN 3 O 3 S[M+H + ]:448.0325,found 448.0332.
Example 9
N-but-3-enyl-7-trifluoromethyl quinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (3 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 8 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ia is obtained by column chromatography separation, wherein the yield is 58%.
1 H NMR(400MHz,CDCl 3 )δ8.30-8.26(m,1H),7.89-7.82(m,2H),7.77-7.74 (m,1H),7.67(d,J＝8.2Hz,2H),7.36(d,J＝8.0Hz,2H),4.13-4.07(m,1H), 3.97-3.92(m,1H),3.49-3.42(m,1H),3.33-3.30(m,1H),3.19-3.12(m,1H), 2.42-2.30(m,4H),2.11-2.02(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.7,159.2, 148.9,142.7,137.5,133.6(q,J C-F ＝32.2Hz),129.6,127.4,126.4,123.9(q,J C-F ＝4.1 Hz),123.6(q,J C-F ＝274.0Hz),123.3,121.7(q,J C-F ＝3.6Hz),45.1,44.1,43.6,23.2, 20.9；HRMS(ESI)m/z calcd for C 20 H 19 F 3 N 3 O 3 S[M+H + ]:438.1094,found 438.1091.
Example 10
N-but-3-enyl-7-methylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under blue light 6W LED lamp strip irradiation. And (3) after the reaction is finished, removing the solvent under reduced pressure, and separating by using column chromatography to obtain a target product 3ja with the yield of 66%.
1 H NMR(400MHz,CDCl 3 )δ7.97(d,J＝8.1Hz,1H),7.72(d,J＝8.2Hz,2H), 7.29(s,1H),7.23(d,J＝8.1Hz,2H),7.17(d,J＝8.1Hz,1H),6.70-6.67(m,1H), 4.22-4.16(m,1H),3.89-3.82(m,1H),3.45-3.29(m,2H),3.20-3.14(m,1H),2.42(s, 3H),2.36(s,3H),2.35-2.28(m,1H),2.04-1.93(m,1H)； 13 C NMR(101MHz,CDCl 3 ) δ160.5,159.8,148.6,145.3,143.5,136.9,129.8,128.2,126.9,126.5,126.1,118.2, 44.9,44.5,42.8,23.8,21.9,21.5；HRMS(ESI)m/z calcd for C 20 H 22 N 3 O 3 S[M+H + ]: 384.1376,found 384.1377.
Example 11
N-but-3-enyl-6-fluoroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (2 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ka is obtained by column chromatography separation, wherein the yield is 72%.
1 H NMR(400MHz,CDCl 3 )δ7.75-7.69(m,3H),7.57-7.53(m,1H),7.39-7.34 (m,1H),7.23(d,J＝8.1Hz,2H),6.42-6.39(m,1H),4.25-4.19(m,1H),3.93-3.86(m, 1H),3.47-3.33(m,2H),3.23-3.17(m,1H),2.42-2.35(m,1H),2.37(s,3H),2.06-1.96 (m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.6(d,J C-F ＝249.1Hz),159.8(d,J C-F ＝ 3.4Hz),159.2(d,J C-F ＝2.1Hz),145.1(d,J C-F ＝1.9Hz),143.6,136.8,129.8,129.2 (d,J C-F ＝8.2Hz),126.9,122.7(d,J C-F ＝24.2Hz),122.0(d,J C-F ＝8.5Hz),111.2(d, J C-F ＝23.6Hz),45.0,44.5,42.8,23.9,21.5；HRMS(ESI)m/z calcd for C 19 H 19 FN 3 O 3 S[M+H + ]:388.1126,found 388.1128.
Example 12
N-but-3-enyl-6-bromoquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, nitrogen was pumped and sealed, and stirred at room temperature for 6 hours under the irradiation of a blue light 6W LED lamp. And after the reaction is finished, removing the solvent under reduced pressure, and performing column chromatography to obtain a target product 3la with the yield of 80%.
1 H NMR(400MHz,CDCl 3 )δ8.17(d,J＝2.3Hz,1H),7.69-7.66(m,3H),7.39 (d,J＝8.7Hz,1H),7.22(d,J＝8.0Hz,2H),6.41-6.38(m,1H),4.25-4.18(m,1H), 3.93-3.88(m,1H),3.47-3.32(m,2H),3.23-3.17(m,1H),2.42-2.34(m,1H),2.37(s, 3H),2.08-1.98(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.3,159.3,147.4,143.6, 137.3,136.7,129.8,128.8,128.7,126.9,122.1,120.0,45.2,44.4,43.1,23.7,21.6； HRMS(ESI)m/z calcd for C 19 H 19 BrN 3 O 3 S[M+H + ]:448.0325,found 448.0332.
Example 13
N-but-3-enylquinazolinone (0.2 mmol), N-benzenesulfonamide pyridinium salt (0.25 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, evacuated of nitrogen and sealed, and stirred under blue light irradiation with a 6W LED lamp at room temperature for 12 hours. And (3) after the reaction is finished, decompressing and removing the solvent, and performing column chromatography separation to obtain a target product 3ab with the yield of 75%.
1 H NMR(400MHz,CDCl 3 )δ8.12-8.08(m,1H),7.85-7.82(m,2H),7.66-7.60 (m,1H),7.54-7.42(m,4H),7.38-7.33(m,1H),6.69-6.65(m,1H),4.24-4.18(m,1H), 3.91-3.83(m,1H),3.48-3.32(m,2H),3.23-3.17(m,1H),2.39-2.32(m,1H), 2.05-1.95(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.5,159.7,148.4,139.9,134.3, 132.7,129.2,126.9,126.8,126.6,126.3,120.6,44.9,44.5,42.9,23.8；HRMS(ESI) m/z calcd for C 18 H 18 N 3 O 3 S[M+H + ]:356.1063,found 356.1061.
Example 14
N-but-3-enylquinazolinone (0.2 mmol), N-p-tert-butylbenzenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, nitrogen gas was pumped and sealed, and the mixture was stirred at room temperature for 12 hours under the irradiation of a blue light 6W LED lamp. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ac is obtained by column chromatography separation with the yield of 69%.
1 H NMR(400MHz,CDCl 3 )δ8.13(dd,J＝8.0,1.0Hz,1H),7.76(d,J＝8.5Hz, 1H),7.67-7.63(m,1H),7.53(d,J＝8.0Hz,1H),7.46(d,J＝8.5Hz,2H),7.37(t,J＝ 7.7Hz,1H),6.57-6.54(m,1H),4.27-4.21(m,1H),3.93-3.86(m,1H),3.48-3.36(m, 2H),3.24-3.18(m,1H),2.43-2.35(m,1H),2.08-1.97(m,1H),1.29(s,9H)； 13 C NMR (101MHz,CDCl 3 )δ160.5,159.8,156.5,148.5,136.8,134.3,126.8,126.6,126.3, 126.2,120.7,44.9,44.5,43.0,35.2,31.1,23.8；HRMS(ESI)m/z calcd for C 22 H 26 N 3 O 3 S[M+H + ]:412.1689,found 412.1693.
Example 15
N-but-3-enylquinazolinone (0.2 mmol), pyridine N-p-chlorobenzenesulfonamide (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, evacuated and sealed with nitrogen, and stirred at room temperature for 12 hours under irradiation of a white light 10W LED bulb. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 3ad is obtained by column chromatography separation, wherein the yield is 73%.
1 H NMR(400MHz,CDCl 3 )δ8.12(dd,J＝8.0,1.2Hz,1H),7.77(d,J＝8.6Hz, 1H),7.67-7.63(m,1H),7.51(d,J＝8.0Hz,1H),7.42-7.36(m,3H),6.74-6.71(m, 1H),4.27-4.21(m,1H),3.93-3.86(m,1H),3.51-3.35(m,2H),3.23-3.17(m,1H), 2.43-2.35(m,1H),2.04-1.94(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.5,159.7, 148.4,139.2,138.3,134.3,129.5,128.4,126.8,126.7,126.3,120.7,44.9,44.6,42.8, 23.8；HRMS(ESI)m/z calcd for C 18 H 17 ClN 3 O 3 S[M+H + ]:390.0674,found 390.0671.
Example 16
N-but-3-enylquinazolinone (0.2 mmol), N-2-thiophenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, evacuated with nitrogen and sealed, and stirred at room temperature for 10 hours under irradiation of a blue light 6W LED lamp strip. And (3) after the reaction is finished, decompressing and removing the solvent, and performing column chromatography separation to obtain a target product 3ae with the yield of 61%.
1 H NMR(400MHz,CDCl 3 )δ8.17(dd,J＝8.0,1.3Hz,1H),7.70-7.66(m,1H), 7.62-7.54(m,3H),7.43-7.39(m,1H),7.06-7.04(m,1H),6.78-6.75(m,1H),4.30-4.25 (m,1H),3.95-3.88(m,1H),3.61-3.54(m,2H),3.46-3.38(m,1H),3.32-3.25(m,1H), 2.46-2.38(m,1H),2.07-1.96(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ160.5,159.8, 148.4,140.8,134.3,132.1,132.0,127.5,126.9,126.7,126.4,120.7,44.9,44.8,42.6, 23.9；HRMS(ESI)m/z calcd for C 16 H 16 N 3 O 3 S 2 [M+H + ]:362.0628,found 362.0628.
Example 17
N-pent-4-enyl quinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (3 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred under blue light 6W LED lamp band irradiation at room temperature for 8 hours. And (3) after the reaction is finished, decompressing and removing the solvent, and performing column chromatography separation to obtain a target product 5aa with the yield of 82%.
1 H NMR(400MHz,CDCl 3 )δ8.21(d,J＝7.9Hz,1H),7.77(d,J＝8.2Hz,2H), 7.72(t,J＝8.2Hz,1H),7.53(d,J＝8.2Hz,2H),7.44(t,J＝7.5Hz,1H),7.28(d,J＝ 8.2Hz,1H),6.57-6.55(m,1H),4.31-4.25(m,1H),3.82-3.75(m,1H),3.43-3.37(m, 1H),3.23-3.17(m,1H),3.02-2.95(m,1H),2.40(s,3H),2.11-1.89(m,3H),1.65-1.55 (m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.5,156.4,146.4,143.4,137.1,134.3, 129.8,126.9,126.8,126.6,120.3,45.5,40.9,39.9,23.4,21.6,20.7；HRMS(ESI)m/z calcd for C 20 H 22 N 3 O 3 S[M+H + ]:384.1376,found 384.1375.
Example 18
N-pent-4-enyl-8-methylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.24 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ba is obtained by column chromatography, wherein the yield is 72%.
1 H NMR(400MHz,CDCl 3 )δ8.05(d,J＝7.5Hz,1H),7.75(d,J＝8.2Hz,2H), 7.54(d,J＝7.2Hz,1H),7.32-7.27(m,3H),6.87-6.84(m,1H),4.22-4.15(m,1H), 3.88-3.82(m,1H),3.45-3.38(m,1H),3.22-3.16(m,1H),3.04-2.96(m,1H),2.49(s, 3H),2.39(s,3H),2.11-2.03(m,1H),1.99-1.93(m,2H),1.63-1.53(m,1H)； 13 C NMR (101MHz,CDCl 3 )δ161.8,155.3,144.9,143.5,136.9,134.9,134.5,129.8,126.9, 126.3,124.5,120.2,45.8,41.2,39.9,23.7,21.5,20.8,17.7；HRMS(ESI)m/z calcd for C 21 H 24 N 3 O 3 S[M+H + ]:398.1533,found 398.1536.
Example 19
N-pent-4-enyl-8-fluoroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, evacuated of nitrogen and sealed, and stirred at room temperature for 12 hours under illumination of a white light 10 watt LED bulb. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ca is obtained by column chromatography separation, wherein the yield is 70%.
1 H NMR(300MHz,CDCl 3 )δ7.87(d,J＝7.7Hz,1H),7.73(d,J＝8.2Hz,2H), 7.37-7.27(m,2H),7.22(d,J＝8.4Hz,2H),6.71-6.67(m,1H),4.20-4.11(m,1H), 3.82-3.73(m,1H),3.35-3.28(m,1H),3.09-2.93(m,2H),2.32(s,3H),2.08-1.85(m, 3H),1.60-1.49(m,1H)； 13 C NMR(75MHz,CDCl 3 )δ160.5(d,J C-F ＝3.4Hz),157.2, 156.4(d,J C-F ＝253.4Hz),143.3,136.8,135.9(d,J C-F ＝11.7Hz),129.7,127.0,126.6 (d,J C-F ＝7.5Hz),122.1(d,J C-F ＝4.1Hz),119.5(d,J C-F ＝18.6Hz),45.6,41.2,40.2, 23.3,21.5,20.7；HRMS(ESI)m/z calcd for C 20 H 21 FN 3 O 3 S[M+H + ]:402.1282,found 402.1283.
Example 20
N-pent-4-enyl-7-methylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 12 hours under blue light 6W LED lamp strip irradiation. After the reaction was completed, the solvent was removed under reduced pressure, and column chromatography was performed to obtain the objective product 5da in 83% yield.
1 H NMR(300MHz,CDCl 3 )δ8.09(d,J＝8.1Hz,1H),7.77(d,J＝8.2Hz,2H), 7.32-7.24(m,4H),6.65(s,1H),4.29-4.20(m,1H),3.81-3.72(m,1H),3.41-3.37(m, 1H),3.22-3.15(m,1H),2.99-2.90(m,1H),2.48(s,3H),2.40(s,3H),2.08-1.89(m, 3H),1.64-1.54(m,1H)； 13 C NMR(75MHz,CDCl 3 )δ161.4,156.4,146.5,145.3, 143.4,137.1,129.8,128.3,126.9,126.6,126.4,117.9,45.5,40.9,39.8,23.5,21.9, 21.5,20.7；HRMS(ESI)m/z calcd for C 21 H 24 N 3 O 3 S[M+H + ]:398.1533,found 398.1536.
Example 21
N-pent-4-enyl-7-fluoroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.26 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 6 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ea is obtained by column chromatography separation, wherein the yield is 77%.
1 H NMR(400MHz,CDCl 3 )δ7.79-7.76(m,1H),7.73(d,J＝8.2Hz,2H), 7.53-7.49(m,1H),7.42-7.37(m,1H),7.26(d,J＝8.2Hz,2H),6.44-6.41(m,1H), 4.27-4.21(m,1H),3.80-3.74(m,1H),3.42-3.36(m,1H),3.23-3.17(m,1H), 2.99-2.92(m,1H),2.38(s,3H),2.10-2.02(m,1H),1.98-1.88(m,2H),1.65-1.55(m, 1H)； 13 C NMR(100MHz,CDCl 3 )δ160.8(d,J C-F ＝3.4Hz),160.6(d,J C-F ＝246.5 Hz),155.6(d,J C-F ＝2.2Hz),143.5,143.1(d,J C-F ＝1.7Hz),137.1,129.8,129.2(d, J C-F ＝8.3Hz),126.9,122.8(d,J C-F ＝24.2Hz),121.5(d,J C-F ＝8.7Hz),111.4(d,J C-F ＝23.7Hz),45.3,41.2,40.0,23.3,21.5,20.6；HRMS(ESI)m/z calcd for C 20 H 21 FN 3 O 3 S[M+H + ]:402.1282,found 402.1283.
Example 22
N-pent-4-enyl-7-chloroquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 8 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5fa is obtained by column chromatography separation with the yield of 81 percent.
1 H NMR(400MHz,CDCl 3 )δ8.11-8.07(m,1H),7.74(d,J＝8.1Hz,2H), 7.47-7.46(m,1H),7.36-7.32(m,1H),7.28(d,J＝7.2Hz,2H),6.32(s,1H), 4.28-4.20(m,1H),3.80-3.73(m,1H),3.42-3.36(m,1H),3.25-3.18(m,1H), 3.00-2.93(m,1H),2.40(s,3H),2.11-1.99(m,1H),1.99-1.89(m,2H),1.66-1.56(m, 1H)； 13 C NMR(101MHz,CDCl 3 )δ160.9,157.7,147.4,143.5,137.1,129.8,128.2, 127.3,127.2,126.9,126.2,118.7,45.2,41.1,40.2,23.2,21.6,20.6；HRMS(ESI)m/z calcd for C 20 H 21 ClN 3 O 3 S[M+H + ]:418.0987,found 418.0991.
Example 23
N-pent-4-enyl-7-bromoquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred under blue light 6W LED lamp strip irradiation at room temperature for 12 hours. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ga is obtained by column chromatography separation, wherein the yield is 71 percent.
1 H NMR(300MHz,CDCl 3 )δ8.02(d,J＝8.5Hz,1H),7.76(d,J＝8.2Hz,2H), 7.66(d,J＝1.7Hz,1H),7.53(dd,J＝8.5,1.7Hz,1H),7.28(d,J＝8.1Hz,2H), 6.32-6.28(m,1H),4.29-4.20(m,1H),3.81-3.72(m,1H),3.44-3.36(m,1H), 3.26-3.17(m,1H),3.02-2.92(m,1H),2.41(s,3H),2.11-1.88(m,3H),1.68-1.57(m, 1H)； 13 C NMR(75MHz,CDCl 3 )δ161.0,157.7,147.4,143.5,137.0,130.0,129.8, 129.4,128.9,128.2,126.9,119.1,45.2,41.1,40.2,23.2,21.6,20.6；HRMS(ESI)m/z calcd for C 20 H 21 BrN 3 O 3 S[M+H + ]:462.0482,found 462.0477.
Example 24
N-pent-4-enyl-7, 8-dimethylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CzIPN (2 mol%), dichloroethane (4 mL) were added to the Schlenk reaction tube, nitrogen gas was evacuated and sealed, and stirred at room temperature for 12 hours under irradiation of a white light 10W LED bulb. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ha is obtained by column chromatography separation, wherein the yield is 63%.
1 H NMR(400MHz,CDCl 3 )δ7.94(d,J＝8.1Hz,1H),7.75(d,J＝8.2Hz,2H), 7.27(d,J＝8.0Hz,2H),7.21(d,J＝8.0Hz,2H),6.72(s,1H),4.24-4.18(m,1H), 3.83-3.76(m,1H),3.44-3.41(m,1H),3.23-3.18(m,1H),3.02-2.95(m,1H), 2.40-2.38(m,9H),2.11-2.02(m,1H),1.98-1.88(m,2H),1.63-1.54(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.9,154.9,144.8,143.4,136.9,132.4,129.8,128.8, 127.0,126.4,123.6,118.2,45.7,40.9,39.8,23.7,21.6,21.0,20.8,13.4；HRMS(ESI) m/z calcd for C 22 H 26 N 3 O 3 S[M+H + ]:412.1689,found 412.1691.
Example 25
N-pent-4-enyl-6-methylquinazolinone (0.2 mmol), N-p-toluenesulfonamide pyridinium salt (0.3 mmol), 4CZIPN (2 mol%), dichloroethane (4 mL) were added to a Schlenk reaction tube, purged with nitrogen and sealed, and stirred at room temperature for 10 hours under blue light 6W LED lamp strip irradiation. After the reaction is finished, the solvent is removed under reduced pressure, and the target product 5ia is obtained by column chromatography separation, wherein the yield is 70%.
1 H NMR(400MHz,CDCl 3 )δ7.96(s,1H),7.75(d,J＝8.2Hz,2H),7.50(d,J＝ 8.3Hz,1H),7.39(d,J＝8.3Hz,1H),7.26(d,J＝8.0Hz,2H),6.64-6.61(m,1H), 4.26-4.19(m,1H),3.80-3.73(m,1H),3.40-3.34(m,1H),3.20-3.14(m,1H), 2.98-2.91(m,1H),2.44(s,3H),2.38(s,3H),2.08-2.00(m,1H),1.97-1.87(m,2H), 1.62-1.52(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ161.5,155.4,144.4,143.4,137.1, 136.9,135.8,129.8,126.9,126.5,126.0,120.0,45.6,40.9,39.8,23.5,21.6,21.4,20.7； HRMS(ESI)m/z calcd for C 21 H 24 N 3 O 3 S[M+H + ]:398.1533,found 398.1536.
The above description is only an embodiment of the present invention, and is not intended to limit the scope of the present invention, and all modifications, equivalents, and flow charts using the content of the present invention, or directly or indirectly applied to other related technical fields are included in the scope of the present invention.
Claims (9)
1. A synthetic method of a sulfonamide-substituted polycyclic quinazolinone compound is characterized in that the reaction is carried out according to the following steps: taking N-alkyl quinazolinone containing an unactivated double bond as a substrate, taking N-sulfonamido pyridine salt as a sulfonamide radical precursor under the catalytic action of a photosensitizer, and synthesizing a sulfonamide-substituted polycyclic quinazolinone new compound by taking quinazolinone through reaction processes comprising radical addition, cyclization reaction, 1, 2-hydrogen migration, single electron transfer and dehydrooxidation in a solvent;
the general reaction formula is as follows:
wherein n =1,2;
r is selected from any one of hydrogen, C1-C4 linear alkane, halogen, C1-C4 linear alkoxy and trifluoromethyl, and the position of a substituent can be at the 5,6, 7 and 8 positions of the quinazolinone mother nucleus;
ar is selected from any one of phenyl, thienyl, p-halophenyl and p-tert-butylphenyl.
2. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound of claim 1, wherein the photosensitizer used is 2,4,5, 6-tetrakis (9-carbazolyl) -isophthalonitrile.
3. The method for synthesizing sulfonamide-substituted polycyclic quinazolinone compound of claim 1, wherein the synthesis reaction is performed at room temperature for 6-12 h.
4. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound of claim 1, wherein the concentration of the reactant N-alkyl quinazolinone is 0.05-0.1mmol/mL.
5. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound according to claim 1, wherein the mass ratio of the N-alkyl quinazolinone to the N-sulfonamidopyridine salt is 1.0 to 2.0.
6. The method of claim 1, wherein the light source is a blue LED strip or a white LED bulb.
7. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound of claim 1, wherein said solvent is dichloroethane.
8. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound of claim 2, wherein the amount of photosensitizer used is 2mol%.
9. The method for synthesizing a sulfonamide-substituted polycyclic quinazolinone compound according to claim 1, wherein the product is obtained by column chromatography separation after the reaction is completed, and the eluent is a mixed solvent of petroleum ether and ethyl acetate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116005178A (en) * | 2023-01-28 | 2023-04-25 | 淮北师范大学 | Synthesis method of 1,2-dihydro quinazoline compound |
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