Heterocyclic Building Blocks-Pyrrolines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2973-17-3,1-Allyl-1H-pyrrole-2,5-dione,as a common compound, the synthetic route is as follows.

General procedure: (All the reactions were performed on 50mg scale of aldehyde.) A reaction mixture containing K2CO3 (80mol%), NHC precatalyst A (15mol%), maleimide 2 (1.5 equiv) and aldehyde 1 (1.0 equiv) in THF (2mL) under argon atmosphere was stirred at 50C for 30min to 2h. When the reaction was complete, the crude reaction mixture was allowed to attain room temperature, followed by filtration of the reaction mixture through a bed of celite. The residue was washed with ethyl acetate (5mL x 3) and the combined filtrate was evaporated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel using solvent gradient of petroleum ether:ethyl acetate to furnish the desired products 4-13, 15-21 in 10-90% yield., 2973-17-3

The synthetic route of 2973-17-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ahire, Milind M.; Mhaske, Santosh B.; Tetrahedron; vol. 74; 16; (2018); p. 2079 – 2084;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.541-59-3,Maleimide,as a common compound, the synthetic route is as follows.,541-59-3

Example 9:conversion of an amine to a maleimide moiety /V-(Methoxycarbonyl)maleimide (37) Methyl chloroformate (0.87 ml_, 11.3 mmol) was added slowly to a solution of maleimide (1.00 g, 10.3 mmol) and /V-methyl morpholine (1.24 ml_, 1 1.3 mmol) in EtOAc (80 ml_) at 0 C and stirred for 1 hr. The precipitate was separated out through filtration through a celite pad and the filtrate concentrated in vacuo. It was attempted to recrystallise the crude oil with hexane: CH2CI2 but no crystallisation occurred. The crude product was redissolved in EtOAc (100 ml_), adsorbed onto silica and purified using column chromatography (Hex: EtOAc 6:4) to yield a white solid (1 .07 g, 67%). 5H (CDCI3, 300 MHz): 6.83 (2H, s, CH-3/4), 3.94 (3H, s, CH3-2′) 8c (CDCI3, 100 MHz): 165.6 (C-2/5), 148.1 (C-1 ‘), 132.3 (C-3/4), 54.2 (C-2’)

541-59-3 Maleimide 10935, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; THE SOUTH AFRICAN NUCLEAR ENERGY CORPORATION LIMITED; UNIVERSITY OF CAPE TOWN; DRIVER, Cathryn Helena Stanford; ZEEVAART, Jan Rijn; PARKER, Mohamed Iqbal; HUNTER, Roger; (67 pag.)WO2016/46793; (2016); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1122-10-7,3,4-Dibromo-1H-pyrrole-2,5-dione,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 2,3-dibromomaleimide23 (1.0 mmol) in CH2Cl2 (20ml) Et3N (2.0mmol) and thiol (2.1mmol) were added under argon atmosphere and stirred for 3 h at room temperature. The reaction mixture was evaporated,and the crude product was purified by flash chromatography to give the desired compound.

1122-10-7, As the paragraph descriping shows that 1122-10-7 is playing an increasingly important role.

Reference£º
Article; Csavas, Magdolna; Miskovics, Adrienn; Szcs, Zsolt; Rth, Erzsebet; Nagy, Zsolt L; Bereczki, Ilona; Herczeg, Mihaly; Batta, Gyula; Nemes-Nikodem, Eva; Ostorhazi, Eszter; Rozgonyi, Ferenc; Borbas, Aniko; Herczegh, Pal; Journal of Antibiotics; vol. 68; 9; (2015); p. 579 – 585;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

151038-94-7, 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1 mmol of doxorubicin, 3 mmol of 6-maleimidocaproyl hydrazide trifluoroacetate, mix 20mL of methanol and 0.01mL of trifluoroacetic acid, in the dark,The nucleophilic addition reaction was carried out at 20 C for 24 h; the obtained system was mixed with ethanol, and then subjected to precipitation and ultrafiltration centrifugation, and the obtained concentrated material was lyophilized. Obtaining maleimide functionalized doxorubicin; 1 mmol of KLAK peptide with a cysteine at the N-terminus, 15 mmol of tris(2-carbonylethyl)phosphoric acid hydrochloride and 10 mL of phosphate buffer solution (concentration: 20 mmol/L, pH 7.4) were mixed, and stirred at 25 C for 1 h; Then add 3 mmol of maleimide functionalized doxorubicin, adding reaction under stirring at 25 C for 2 h; the obtained system was allowed to stand at 4 C for 22 h, and then subjected to ultrafiltration centrifugation. The resulting concentrated material is lyophilized, an anti-tumor peptide-doxorubicin derivative is obtained., 151038-94-7

151038-94-7 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate 23509306, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; Beihua University; Guan Xingang; Xia Wei; Chen Li; (11 pag.)CN109675051; (2019); A;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55750-49-7,Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

55750-49-7, A solution of 62 (2.12 g, 5.4 minol), acetic acid (1.5 mL) and palladium-on-carbon (0.2 g,10% w/w) in methanol (30 mL) was stirred at room temperature under a hydrogenatmosphere for 90 minutes. The mixture was then filtered through Celite and the solution concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (1.36 g, 8.1 minol) in saturated aqueous sodium bicarbonate (50 mL) at 0 C, and the mixture stirred at 0 C for 10 minutes. Acetonitrile (25mL) was then added and the mixture stirred at room temperature for 90 min. The mixture was then extracted with dichloromethane (3 x), the combined organic layers dried over anhydrous magnesium sulfate, filtered and the solution concentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2) afforded the title compound 63 (1.43 g, 78%) as a yellow oil. [aID237 = + 11.1 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.31-1.38 (2H, m, H-4?), 1.44 (9H, s, Boc), 1.59-1.67 (3H, m, Hb-3?, H-5?), 1.79-1.83 (1H, m,Ha3?), 3.51 (2H, t, J = 7.2 Hz, H-6?), 3.74 (3H, s, OMe), 4.27 (1H, m, H-2?), 5.08 (1H, d, J= 7.9 Hz, NH), 6.70 (2H, s, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 22.4 (CH2, C-4?), 28.0(CH2, C-5?), 28.3 (3 x CH3, Boc), 32.1 (CH2, C-3?), 37.3 (CH, C-6?), 52.2 (CH3, OMe), 53.2(CH, C-2?), 79.8 (C, Boc), 134.1 (2 x CH, C-3, C-4), 155.3 (C, Boc), 170.7 (2 x C, C-2, C-5), 173.1 (C, C-i?); vmax (cm1) 3374, 2952, 1698, 1365, 1160, 828, 694; HRMS-ESI[M+Na] Calcd. for C16H24N2O6Na 363.1527, found 363.1528.

As the paragraph descriping shows that 55750-49-7 is playing an increasingly important role.

Reference£º
Patent; SAMMUT, Ivan Andrew; HARRISON, Joanne Clare; HEWITT, Russell James; READ, Morgayn Iona; STANLEY, Nathan John; WOODS, Laura Molly; KUEH, Jui Thiang Brian; JAY-SMITH, Morgan; SMITH, Robin Andrew James; GILES, Gregory; LARSEN, Lesley; RENNISON, David; BRIMBLE, Margaret Anne; LARSEN, David Samuel; (209 pag.)WO2017/95237; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6913-92-4, Example 26 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1-benzyl-4-hydroxy-pyrrolidin-3-yl)-amide Preparation of 4-Amino-1-benzyl-pyrrolidin-3-ol Step 1: To an ice-cooled solution of 26a (4.77 g, 30 mmol), 98% H2SO4 (1.95 mL), H2O (4.5 mL) and acetone (30 mL) was added 85% mCPBA (7.91 g, 39 mmol) with stirring. The mixture was allowed to react for 48 hrs at r.t. Acetone was evaporated and the mixture was neutralized with 1N aq. NaOH and extracted with toluene. The organic phase was dried over anhy. MgSO4 and evaporated. The residue was purified by column chromatography (EA:PE=1:4) to provide 26b (2.0 g, 38%).

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; Xcovery, Inc.; US2009/76005; (2009); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

1122-10-7, 3,4-Dibromo-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 12 Preparation of Di-dansyl-cystamine-maleimide A round bottomed flask was charged with di-dansyl cystamine (100 mg, 0.16 mmol), TCEP (46 mg, 1 eq) and MeOH (10 ml). The reaction mixture was stirred at ambient temperature under argon for 3 hrs. Dibromomaleimide (36 mg, 0.9 eq), in MeOH (5 ml) was then added to the reaction mixture. After 30 mins NaOAc (56 mg, 4 eq), was added to the reaction mixture and the solvent evaporated in vacuo. The residue was worked up with DCM and brine. The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-20% EtOAc-DCM) afforded the desired compound as a yellow gum (40 mg, 40%). 1HNMR (CDCl3, 600 MHz), delta8.5 (2H, d J 8.5 Hz aromatic H’s), delta8.2 (4H, m aromatic H’s), delta7.53 (1H, s CONH), delta7.46 (4H, m, aromatic H’s), delta7.1 (2H, d, J=7.4 Hz aromatic H’s), delta5.65 (2H, t, J 6.27 SO2NH), delta3.3 (4H, t, J 6.0 SCH2), delta3.17 (4H, q, J 6.0 NHCH2), delta2.8 (12H, s NCH3); 13CNMR (CDCl3, 150 MHz), 6165.9, 152.0, 136.5, 134.7, 130.7, 129.94, 129.85, 129.62, 129.57, 128.63, 123.3, 118.8, 115.4, 45.5, 43.6, 31.8; IR (cm-1) 3288 (br) 1720 (s) MS (Na+) m/z relative intensity: 736 (M, 100); Exact mass calculated for [C32H35N5O6NaS4] requires m/z 736.1368. Found 736.1390 (Na+)., 1122-10-7

The synthetic route of 1122-10-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCL Business Plc; Smith, Mark; Caddick, Stephen; Baker, James; Chudasama, Vijay; (80 pag.)US9295729; (2016); B2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17057-04-4,4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid,as a common compound, the synthetic route is as follows.

General procedure: Equimolar quantities of maleimide (2) and nitrones (5a-k and 6a-k) were refluxed in toluene (20 ml) and ethyl alcohol (5 ml) for 8-10 h (TLC monitoring using petroleum ether and hexane 1:1) followed by cooling with addition of dry ether. The products (7a-k and 8a-k) were separated out after filtration and recrystallized from toluene and petroleum ether mixture (1:1) to yield cis-isomers (7aa-7ka and 8aa-8ka). The mother liquor on further work up provided trans-isomers which were recrystallized from ethanol and diethyl ether mixture (1:1) (7aa’-7ka’ and 8aa’-8ka’) (Fig. 3).7 These stereoisomers were characterized by their 1H NMR, IR and mass spectra in addition to their melting points and elementary analysis. These stereoisomers have identical IR spectra and elemental analysis but differ in their melting points, 1H NMR and mass spectra., 17057-04-4

As the paragraph descriping shows that 17057-04-4 is playing an increasingly important role.

Reference£º
Article; Anand, Preet; Singh, Baldev; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 521 – 530;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

1122-10-7, 3,4-Dibromo-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(Indolin-3-yl)ethanole 2a (1.700 g, 10.4 mmol) and Et(iPr)2N(3.5 mL, 20 mmol) were added to solution of 3,4-dibrommalemide 1 (2.540 g, 10 mmol) in dry DMF (5 mL). The reaction mixture was left to stir overnight at 50 C. The cooled to rt reaction mixture was diluted with EtOAc (100 mL), washed with water (200 mL), brine (50 mL), dried, and evaporated. The residue was chromatographed (33.3% EtOAc/petroleum ether) to give 4a as a red amorphous solid (2.642 g, 7.8 mmol, 80%); mp 137-139 C; Rf (50% EtOAc/petroleumether) 0.35; vmax 1767, 1715, 1624, 1591 cm-1; deltaH (400 MHz, DMSO-d6): 1.60-1.69 (2H, m), 1.89-1.97 (2H, m), 3.52-3.55 (2H, m),4.00-4.05 (1H, m), 4.37-4.42 (1H, m), 6.95 (1H, d, J 8.0 Hz), 6.99(1H, t, J 7.5 Hz), 7.16 (1H, t, J 7.6 Hz), 7.25 (1H, d, J 7.5 Hz), 11.02 (1H,s); deltaC (100 MHz, DMSO-d6): 36.5, 38.3, 58.7, 59.5, 91.0 (q), 115.8,122.8, 123.9, 126.3, 136.4 (q), 141.7 (q), 142.0 (q), 166.8 (C=O), 167.1(C=O); HRMS [MNa]+, found: 358.9987, [C14H13BrN2O3Na] requires 359.0007.

1122-10-7, As the paragraph descriping shows that 1122-10-7 is playing an increasingly important role.

Reference£º
Article; Simonov, Alexander Y.; Bykov, Evgeny E.; Lakatosh, Sergey A.; Luzikov, Yury N.; Korolev, Alexander M.; Reznikova, Marina I.; Preobrazhenskaya, Maria N.; Tetrahedron; vol. 70; 3; (2014); p. 625 – 630;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

55750-49-7, Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

55750-49-7, A solution of 82 (278 mg, 0.55 minol) in Tesser?s Base (20 mL, i,4-dioxane/methanol/4M NaOH, 30:9:1 v/v) was stirred at room temperature for 10 minutes. The solution was then concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (163 mg, 0.66 minol) in saturated aqueous sodium bicarbonate (14 mL), and the mixture stirred at room temperature for 5 minutes. Themixture was then extracted with dichloromethane (3 x), the combined organic layers dried over anhydrous magnesium sulfate, filtered and the solution concentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2) afforded the title compound 83 (100 mg, 50%) as a yellow oil. [aID232 = -1.0 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.33-1.41 (2H, m, H-3?), 1.44 (9H, s, Boc), 1.59-1.69 (2H, m, H-4?), 1.81-1.95(2H, m, H-2?), 2.39 (3H, s, 3?-Me), 3.51 (2H, t, J = 7.2 Hz, H-5?), 4.97-5.01 (iH, m, H-i?),5.09 (iH, d, J = 7.4 Hz, NH), 6.69 (2H, 5, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 11.5 (CH3, 3?-Me), 22.4 (CH2, C-3?), 27.9 (CH2, C-4?), 28.3 (3 x CH3, Boc), 33.4 (CH2, C-2?),37.2 (CH2, C-5?), 48.0 (CH, C-i?), 80.4 (C, Boc), 134.1 (2 x CH, C-3, C-4), i55.0 (C, Boc),i67.i (C, C-3?), i70.8 (2 x C, C-2, C-5), 179.1 (C, C-5?); Vmax (cm1) 3336, 2925, i702,1514, i367, ii64, 828; HRMS-ESI [M+Na] Calcd. for C17H24N4O5Na 387.i639, found387. i652.

The synthetic route of 55750-49-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SAMMUT, Ivan Andrew; HARRISON, Joanne Clare; HEWITT, Russell James; READ, Morgayn Iona; STANLEY, Nathan John; WOODS, Laura Molly; KUEH, Jui Thiang Brian; JAY-SMITH, Morgan; SMITH, Robin Andrew James; GILES, Gregory; LARSEN, Lesley; RENNISON, David; BRIMBLE, Margaret Anne; LARSEN, David Samuel; (209 pag.)WO2017/95237; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem