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Limited Quantity
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Structure of 13925-00-3 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
2
[ 110-85-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 109-97-7 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[6] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
3
[ 13961-37-0 ]
[ 13925-00-3 ]
Reference:
[1] Journal of Organic Chemistry, 1959, vol. 24, p. 691
4
[ 107-15-3 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[4] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
5
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
6
[ 56-87-1 ]
[ 50-99-7 ]
[ 109-08-0 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 15707-23-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372
7
[ 110-85-0 ]
[ 288-32-4 ]
[ 290-37-9 ]
[ 616-47-7 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
Reference:
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
15
[ 123-84-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
[ 15707-23-0 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
16
[ 56-45-1 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 13925-03-6 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 4332 - 4335
17
[ 492-62-6 ]
[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
18
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
19
[ 13925-00-3 ]
[ 22047-25-2 ]
Yield
Reaction Conditions
Operation in experiment
66 %Spectr.
With tert.-butylhydroperoxide In water at 60℃; for 12 h;
General procedure: A 15‐mL RBF was charged with substrate (0.5 mmol),MnOx‐N(at)C catalyst (1 mg, pyrolysis at 600 °C) and TBHP (1.5mmol, 65percent in H2O). The flask was then sealed, and the mixturewas heated at 60 °C for 12 h. The reaction was cooled to roomtemperature and diluted with ethyl acetate (4 mL), before beingcentrifuged at 10000 r/min for 1 min to separate the catalyst.The supernatant was removed and the catalyst waswashed with ethyl acetate (5 × 4 mL). The supernatant wassubsequently combined the ethyl acetate wash solutions andevaporated to dryness to give a residue, which was purified byflash column chromatography over silica gel (ethyl acetate/n‐hexane = 1:10, v/v).
Reference:
[1] Chinese Journal of Catalysis, 2016, vol. 37, # 8, p. 1216 - 1221
20
[ 13925-00-3 ]
[ 98-97-5 ]
Reference:
[1] Journal of Organic Chemistry, 1959, vol. 24, p. 691
[2] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
21
[ 13925-00-3 ]
[ 98-96-4 ]
Reference:
[1] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
22
[ 13925-00-3 ]
[ 6164-79-0 ]
Reference:
[1] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
23
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
24
[ 492-62-6 ]
[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
25
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
26
[ 56-87-1 ]
[ 50-99-7 ]
[ 109-08-0 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 15707-23-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
EXAMPLE 3 With the same catalyst and reaction conditions as those of Example 1, 15.8 grams of ethylpyrazine were obtained by the feeding of 20 grams of N-(2-butylhydroxy)ethylenediamine for 1 hour. Gas chromatographic analysis gave ca. 100percent conversion and 96.4percent selectivity on ethylpyrazine.
16,17,18,19,28,29-hexahydro-4-O-acetyl-11-acetoxy-3-[2-ethyl-4-(2,4,6-trimethylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-11,15-dideoxo-1,15-oxy-rifamycin[ No CAS ]
[ 13961-37-0 ]
Yield
Reaction Conditions
Operation in experiment
With sodium carbonate; acetic acid; In ethanol; dichloromethane;
EXAMPLE 41 In the same manner as outlined in Examples 15 and 20, 3-[2-ethyl-4-(2,4,6-tri-methylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-15-deoxo-1,15-oxy-rifamycin SV, (isomer A), mp 125°-128°, is converted to 16,17,18,19,28,29-hexahydro-4-O-acetyl-11-acetoxy-3-[2-ethyl-4-(2,4,6-trimethylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-11,15-dideoxo-1,15-oxy-rifamycin SV, mp 152°-155°, MW: 1100 (found: MS); C62 H89 N3 O14. The starting material can be prepared, for example, in the following way: A mixture of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (15 g), platinum oxide (800 mg), ethanol (150 ml) and acetic acid (1.5 g) is hydrogenated at 45 psi for 8 hours at room temperature. It is filtered and the filtrate concentrated to an oil which is taken up in methylene chloride, treated with sodium carbonate for 0.5 hour, filtered and concentrated to dryness to white solid 2-ethylpiperazine, mp 56°-57°.
from <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> and methyl 4-chlorobenzoate there is obtained 4'-chloro-2-(2-pyrazinyl)-propiophenone, m.p. 85°;
from <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> and methyl 2,4-dichlorobenzoate there is obtained 2',4'-dichloro-2-(2-pyrazinyl)-propiophenone as an oil.
With N-Bromosuccinimide; potassium carbonate; dibenzoyl peroxide; In tetrachloromethane;
EXAMPLE 1 2-(1-Hydroxyethyl)pyrazine (100) 21.6 g of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (101) was dissolved in 300 ml of carbon tetrachloride and 35.6 g of N-bromosuccinimide added; J. Org. Chem., 37, 511(1972). The mixture was heated to 75° C. and 1.5 g of dibenzoyl peroxide was added in one portion. Heating was continued for 4 hours after which the mixture was cooled and filtered into 500 ml of a 10percent potassium carbonate solution. This mixture was rapidly stirred until no 2-(1-bromoethyl)pyrazine remained (TLC silica gel/1:1 ethyl aqueous solution was acidified to pH 6, concentrated to 200 ml and continuously extracted with ethyl acetate for two days. The ethyl acetate was removed at reduced pressure and the residue distilled, giving 18.6 g of product (100). b.p. 112°-3° (13 mm). UV H2 O max: 264 (3.85), 268 (3.82). 13 C NMR: 159.75, S(C2); 144.52, D, 143.99, D, 142.51, D (C3, C5, C6); 69.20, D (CHOH); 23.11, Q (CH3).
With N-Bromosuccinimide; sodium sulfite; dibenzoyl peroxide; In methanol; tetrachloromethane; water;
EXAMPLE 23 2-(1-Sulfonylethyl)pyrazine sodium salt (2300) 5.4 g of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> was dissolved in 100 ml of carbon tetrachloride and 8.9 g of N-bromosuccinimide added. This mixture was heated to 70°-5° C., 0.5 g dibenzoyl peroxide added and the mixture refluxed for 3 hours. It was then cooled, filtered and the filtrate concentrated in vacuo. To the resultant oil was added 10 g of sodium sulfite/100ml of water and the mixture refluxed for 3 days. It was then cooled, washed with chloroform and freeze-dried. The resultant solid was taken up in 200 ml of methanol, filtered and the filtrate concentrated. It was purified by gel permeation chromatography (Biogel P-2/water) and freeze-dried to give 9.2 g product (2300). It was recrystallized from methanol, m.p. 258°-62°. UV H2 O max: 203 (3.90), 267 (3.87), 272 (3.85). 13 C NMR: 153.54, S (C2); 145.76, D, 144.97, D, 144.14, D (C3, C5, C6); 61.14, D (--CH--); 15.18, Q (CH3).
2-{1-[2-(2-azetidin-1-yl-ethyl)-5-methoxy-3H-inden-1-yl]-ethyl}-pyrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A mixture of (5-methoxy-1-oxo-indan-2-yl) -acetic acid 19a.1 (1 g, 4.5 mmol), EDCI (949 mg, 5 mmol), HOBt (1.5 g, 11.3 mmol) and DIEA (1.7 mL, 9 mmol) in 20 mL dichloromethane was stirred at room temperature for 30 min. Pyrrolidine (483 mg, 6.8 mmol) was added and the resulting reaction mixture was stirred at room temperature for 2 hr. Water was added and the organic layer separated, dried over MgS04, filtered and concentrated to afford 5-methoxy-2-(2-oxo-2-pyrrolidin-l-yl-ethyl)-indan-l-one 21a in 61 percent yield. (MH+ = 274) A solution of s-methoxy-2- (2- oxo-2-pyrrolidin- I -yl-ethyl)-indan- I -one 21a (700 mg, 2.56 mmol) in 5mL of THF and 2 mL of dichloromethane was added dropwise to a mixture of LiAlH4 (150 mg, 3.9 mmol) in 5 mL THF at 0 °C. The resulting reaction mixture was stirred for 20 min and then refluxed for 3 hrs. The reaction mixture was cooled to room temperature and carefully quenched by the sequential addition of H2O, 15percent NaOH and H20. The mixture was stirred for half an hour, and the solid was filtered off using a celite pad and washed with excess THF. The combined filtrates were dried over MgS04 and concentrated to afford 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-ol 21b as a white solid (421 mg, 63percent yield). (MH+ = 262.1) A mixture of 5-methoxy-2- (2-pyrrolidin-1-yl-ethyl)-indan-1-ol 21b(400 mg, 1.5 mmol), diphenylmethanone (1.4 g, 1.5 mmol) and KOtBu (421 mg, 3.8 mmol) in toluene (10 mL) was heated at 120 °C under N2 atmosphere for 3 hrs. The cooled mixture was poured into ice (10 g) and extracted with 10percent HCI until the HCI solution was colorless. The combined acid extracts were washed with EtOAc and added dropwise with stirring into 28percent NH40H (10 mL) and ice. This basic solution was extracted with EtOAc (3 x 10 mL). The combined organic layers were washed with brine, dried over MgS04 and concentrated to give 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-one 21c as an oil (240 mg, 62percent yield). (MH+ = 260) Alternatively the oxidation from the substituted indan-1 -ol to the substituted indan-1-one may use chromium (VI) oxide as reagent. A mixture of pyridine (1.5 mL) and dichloromethane (25 mL) was stirred at 0°C for 15 min. Chromium (VI) oxide (900 mg, 9 mmol) was added and the mixture was stirred for an additional 15 min at 0 °C, allowed to warm to room temperature and stirred for an additional hour at room temperature. A solution of2-[2-(3,3-difluoro-pyrrolidin-l-yl)-ethyl]-indan-l-ol (405 mg, 1.5 mmol) was added and stirring continued for 15 min. After decanting, the dichloromethane layer was washed with water and dried over MgS04. Upon concentration 301 mg of the 2-[2-(3,3- difluoro-pyrrolidin-1-yl) -ethyl]-indan-1-one was obtained as an oil (76percent) and used in the next step without further purification. (MH(at) = 266) A solution of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (100 mg, 0.9 mmol) in THF (2 mL) was added dropwise to a mixture of LDA (0.41 mL, 0.82 mmol, 2M) in THF (3 mL)at 0 °C. A solution of 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-one 21c (100 mg, 0.41 mmol) in THF (2 mL) was added dropwise and the resulting mixture was stirred at 0 °C for 1 hr. Water (10 mL) was added to quench the reaction followed by EtOAc (10 mL) and NH40H (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 3mL). The combined organic layers were concentrated and the residue was dissolved in 4 mL of 20percent HCI and the resulting mixture was stirred at room temperature for 2 hours. The mixture was then poured onto 10 g of ice and 4 mL of NH40H was added dropwise. The resulting mixture was stirred and allowed to warm to room temperature. The organic layer was separated and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were dried over MgS04 and concentrated. Preparative HPLC chromatography afforded 2- {1 1-[2-(2-azetidin-1-yl-ethyl)-5-methoxy-3H-inden-1-yl]-ethyl}- pyrazine 21-1. (MH+=336.1) The following compounds were made according to this procedure: No R3 R1 NR5aR5b R2b MW MH+ (method 2) 21-1 OCH3 Pyrazin-2- yl Azetidin-1-yl CH3 335.45 336.1 3.947 21-2 OCH3 Pyrazin-2- Azetidin-1-yl (R) CH3 335.45 336.1 3.941 yl Profile 7 21-3 OCH3 Pyrazin-2- Azetidin-1-yl (S) _CH3 335.45 336.1 3.974 yl Profile? 21-4 OCH3 Pyrazin-2- yl Pyrroydin-1- yl CH3 349.48 350.1 4.960 21-5 OCH3 Pyrazin-2-yl Pyrrolidin-1- yl H 335.45 336.1 3.749 21-6 OCH3 Pyridazin- Pyrrolidin-1- 335.45 336.1 3.500 3-yl yl 21-7 Pyrazin-2- Pyrrolidin-1- 305.42 306.1 3.673 yl yl 21-8 Pyridazin- Pyrrolidin-l- H 305.42 306.1 3.473 3-yl yl 21-9 OCH3 Pyrazin-2- Morpholin-4- H 351.45 352.1 3.610 yl yl 21- 10 H Pyrazin-2- (at)etidin-1-yl H 291.40 292.1 3.585 21- Pyrazin-2- 3,3-Difluoro- H 309.4 310 3.605 11 yl pyrrolidin-1-yl 21- Pyrazin-2- 3-Fluoro- 341.1 342.1 3.868 12 yl azetidin-1-yl 341.1 342.1 3.868
With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 2585.81 Torr; for 7h;
To a stirred mixture of 2-<strong>[13925-00-3]ethyl pyrazine</strong> (1.0 g, 0.0092 mol., 1.0 eq) in ethanol (20 ml), 10percent Pd on carbon (0.1 g, 50percent wet) was added and stirred at rt under H2 atmosphere at 50 Psi for 7 h. After TLC showed completion of starting material, the mixture was filtered through Celite® bed and washed with ethanol (10 mL). The filtrate was concentrated to afford 2-ethyl piperazine (0.91 g, 91percent).
With tert.-butylhydroperoxide; In water; at 60℃; for 12h;
General procedure: A 15?mL RBF was charged with substrate (0.5 mmol),MnOx?N(at)C catalyst (1 mg, pyrolysis at 600 °C) and TBHP (1.5mmol, 65percent in H2O). The flask was then sealed, and the mixturewas heated at 60 °C for 12 h. The reaction was cooled to roomtemperature and diluted with ethyl acetate (4 mL), before beingcentrifuged at 10000 r/min for 1 min to separate the catalyst.The supernatant was removed and the catalyst waswashed with ethyl acetate (5 × 4 mL). The supernatant wassubsequently combined the ethyl acetate wash solutions andevaporated to dryness to give a residue, which was purified byflash column chromatography over silica gel (ethyl acetate/n?hexane = 1:10, v/v).
With hydrogenchloride; In water; at 70℃; for 0.5h;
A three-necked reactor equipped with a stirrer, an air tube or a dropping funnel was placed in a water bath, and glacial acetic acid 800 mL (820 g) and 37percent hydrochloric acid 80 mL (96 g) were added. After stirring and mixing, 86.4 g of natural <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> was added dropwise, and the mixture was stirred at 70 ° C for 0.5 h. Then, benzoyl peroxide was added to pass chlorine gas at 75 ° C, and the mixture was neutralized and then dichlorocide was used. Methane extraction and concentration gave the intermediate product 1,1-dichloroethyl-2-pyrazine 115 g in an amount of 80percent. The intermediate product 1,1 -dichloroethyl-2-pyrazine 115g and dimethyl sulfoxide 22g were added to a saturated sodium bicarbonate solution for hydrolysis, and then heated to 80 ° C for 6 h, then cooled and extracted to freeze and precipitate. A solid natural 2-acetylpyrazine 57 g (93percent) yield of 60percent was obtained.
methyl 4-phenyl-1-[1-(pyrazin-2-yl)ethyl]isoquinoline-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
27%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; dibenzoyl peroxide; at 100℃; for 2h;Sealed tube; Inert atmosphere;
General procedure: A sealed tube was charged with the vinyl isocyanide 1 (0.2 mmol, 1 equiv), DBU (30 molpercent, 0.06 mmol), BPO (0.4 mmol, 2 equiv) and the alkane (5 mL). The reaction tube was charged with argon three times and the mixture then stirred at 100 °C for 2 h. EtOAc (10 mL) and saturated NaHCO3 solution (10 mL) were added, the organic layer was separated and the aqueous phase was extracted with EtOAc (2 × 10mL). The combined organic layers were washed with H2O (2 × 10 mL) and brine (1 × 10 mL), then dried over anhydrous Na2SO4. The solvent was removed and the resulting residue purified by silica gel column chromatography to afford the desired product 2 or 3.
2-((3-ethylpyrazin-2-yl)methyl)isoindoline-1,3-dione[ No CAS ]
2,2'-((3-ethylpyrazine-2,5-diyl)bis(methylene))bis(isoindoline-1,3-dione)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
16%
With dilauryl peroxide; trifluoroacetic acid; In 1,2-dichloro-ethane; for 5h;Inert atmosphere; Reflux;
General procedure: A magnetically stirred solution of xanthate (2.0 equiv) and pyrazine (1.0 equiv) in 1, 2-dichloroethane (1.0mmol/mL according to the xanthate) was refluxed for 15min under a flow of nitrogen. Then dilauroyl peroxide (DLP) was added portionwise (20mol percent according to the xanthate) every hour until total consumption of one substrate. The reaction mixture was then cooled to room temperature and the solvent was evaporated under reduced pressure. Unless otherwise specified, the crude product was purified by flash chromatography on silica gel.
(2-ethylpyrazinyl)(4-methylphenyl)sulfide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
With N-Bromosuccinimide; di-tert-butyl peroxide; Bathocuproine; nickel(II) acetate tetrahydrate; In fluorobenzene; at 140℃; for 24h;Inert atmosphere;
Under nitrogen protection,4-methylthiophenol 2a (0.5 mmol),Ni (OAc) 2.4H2O (0.025 mmol),BC (0.025 mmol),NBS (0.025 mmol),TBP (0.5 mmol),<strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> 1 p (15 mmol) and fluorobenzene (0.5 mL) were added to the reaction tube. Stir at 140 C for 24 hours. After stopping the reaction, cool to room temperature, evaporate the solvent and separate by column chromatography. The volume ratio (mL / mL) of the eluent used is ethyl acetate: petroleum ether = 0: 100 ~ 1:10 to obtain (2-ethyl Pyrazinyl) (4-methylphenyl) sulfide 3pa, yield 53%.
With sodium hydroxide In water monomer at 120℃; for 1h; Sealed tube;
Preparation of Maillard reaction products derived from Met/Glcmodel and MG-ARP model
General procedure: Aqueous solutions of Met/Glc (each reagent at 0.2 mol/L) and MG-ARP model (0.2 mol/L) were prepared, and their pH values were adjusted to 7.5 ± 0.1 with NaOH (6 mol/L). The model solutions were heated in sealed vials at 100 ± 1, 120 ± 1, or 130 ± 1 °C for different times (0, 30, 60, 120, 180, and 240 min) with continuous stirring. Meanwhile, a 0.2 mol/L solution of Met alone was treated under the same conditions as the control. The final reaction products derived from the above models were cooled in ice water for further analysis.
With sodium hydroxide In water monomer at 120℃; for 1h; Sealed tube;
Preparation of Maillard reaction products derived from Met/Glcmodel and MG-ARP model
General procedure: Aqueous solutions of Met/Glc (each reagent at 0.2 mol/L) and MG-ARP model (0.2 mol/L) were prepared, and their pH values were adjusted to 7.5 ± 0.1 with NaOH (6 mol/L). The model solutions were heated in sealed vials at 100 ± 1, 120 ± 1, or 130 ± 1 °C for different times (0, 30, 60, 120, 180, and 240 min) with continuous stirring. Meanwhile, a 0.2 mol/L solution of Met alone was treated under the same conditions as the control. The final reaction products derived from the above models were cooled in ice water for further analysis.
With anhydrous Sodium acetate at 175℃; for 7h; Overall yield = 0.6 g;
2 Example 2
To 120 g of serine were added 23.4 g of sodium acetate and 120 g of coconut oil. The resulting reaction mixture was then heated for 7 h at 175 °C while stirring. The resulting water was steadily distillated off. After 7 h the reaction mixture was cooled to 80 °C and 80 mL water were added. The product was distilled off together with water at 120 °C and normal pressure. The obtained distillate was extracted with 200 mL ethyl acetate. The organic phase was finally concentrated under reduced pressure (70 mbar, 30 °C) to give 0.6 g of the following alkylpyrazines. GC Analysis (FID, without standard, DB-1 , 60-9-240°): 21 % 2.6-diethylpyrazine, 17.7 % pyrrol, 15.6 % ethylpyrazine, 12.0 % A/-(2-hydroxyethyl)-pyrrol, 4.2 % 2,3-dimethyl-5- ethylpyrazine, 3.1 % 2-ethyl-5-methylpyrazine, 3 % 2,3-diethyl-5,6-dimethylpyrazine, 2.1 % 2-ethyl-3-methylpyrazine, 1.6 % 2,5-diethyl-pyrazine, 1.1 % 2-ethyl-3,5,6- trimethylpyrazine, 0.7 % methylpyrazine, 0.4 % 5-isopropyl-2,3-dimethyl-pyrazine.