Category: 30727-21-0

New synthesis of the amino acid (+-)-cucurbitine was written by Monteiro, Hugo J.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1973.Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate The following contents are mentioned in the article:

Bromination of Et 2,3-dioxo-4-piperidine carboxylate (I; X = H) gave 95% of the 4-bromo derivative (I; X = Br) which with NaN3 in refluxing MeO(CH2)2OMe gave 80% of the azido derivative (I; X = N3). I (X = Br, N3) in CHCl3 with AcOOH underwent ring contraction to 60-80% of the corresponding oxopyrrolidines (II; R = O). II (X = N3, R = O) with Et3O+BF4- gave the imino ether (III). Quant. B2H6 reduction of III gave 40% of the azidopyrrolidine (II; X = N3, R = H2), which underwent catalytic hydrogenation (PtO2) to give (±)-cucurbitine Et ester (II; X = NH2, R = H2) which on hydrolysis gave 70% (±)-cucurbitine. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate).

Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of methyl 1-(3,4-dichlorobenzyl)hexahydro-2,3-dioxo-4-pyridinecarboxylate was written by Schwan, Thomas J.;Gray, Joseph E.;Wright, George C.. And the article was included in Journal of Pharmaceutical Sciences in 1979.Safety of Ethyl 2,3-dioxopiperidine-4-carboxylate The following contents are mentioned in the article:

Me 1-(3,4-dichlorbenzyl)hexahydro-2,3-dioxo-4-pyridinecarboxylate (I) was prepared by alkylation of Me hexahydro-2,3-dioxo-4-pyridinecarboxylate with α,3,4-trichlorotoluene. I was active against pathogenic yeast species, some dermatophytic fungi and Aspergillus niger. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0Safety of Ethyl 2,3-dioxopiperidine-4-carboxylate).

Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Safety of Ethyl 2,3-dioxopiperidine-4-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mechanism of local anesthetic action. 1. Receptor problem was written by Schultz, Otto E.;Ziegler, A.. And the article was included in Pharmazie in 1970.COA of Formula: C8H11NO4 The following contents are mentioned in the article:

Furfuryl alc. was treated 1 hr at -5° with PBr3 and the product treated with MeNH2 and alc. NaI 72 hr at 100-20° to give I. Treatment of I with HBr-HOAc gave a ring-opened product which was cyclized with KOH to give 63% II. Similarly prepared were 10 other compounds including III, IV, V, VI, and VII. The local anesthetic activity of these compounds vs. procaine-HCl (III) was determined III had 80% of the VIII activity. The mechanism of local anesthetic activity is discussed. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0COA of Formula: C8H11NO4).

Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.COA of Formula: C8H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Preparation of Δ¹-pyrroline-2-carboxylic acid and a new proline synthesis was written by Hasse, Kurt;Wieland, Alfred. And the article was included in Chemische Berichte in 1960.HPLC of Formula: 30727-21-0 The following contents are mentioned in the article:

2,3-Dioxopiperidine-4-carboxylic acid Et ester (I), obtained by condensation of 2-pyrrolidone (II) with (CO₂Et)₂ (III), was converted by hydrolysis to H₂N(CH₂)₃COCO₂H.HCl (IV) and this hydrogenated to yield DL-proline (V). K (10 g.) dissolved in 100 cc. absolute EtOH, the solution evaporated in vacuo, the residue dissolved in 200 cc. Et₂O, the solution treated with 25 cc. II and 50 cc. III in 50 cc. Et₂O, the mixture treated after 24 hrs. with 100 cc. 1:4 HCl, and the Et₂O phase concentrated gave 90% [EtO₂C(CH₂)₃NHCO]₂ (VI), m. 106° (H₂O or EtOH). VI (1 g.) in 5 cc. 6N HCl heated 1 hr. at 80° and concentrated gave [HO₂C(CH₂)₃NHCO]₂, m. 210°. II condensed in the usual manner with III, the mixture acidified with HCl, and the Et₂O phase evaporated in vacuo at 120° gave 3-ethoxalyl-2-pyrrolidone (VII), m. 132° (EtOH). 3-Oxalyl-2-pyrrolidone (VIII) (0.75 g.) and 20 cc. alc. HCl kept 36 hrs. at room temperature and evaporated in vacuo yielded VII, m. 131-2° (C₆H₆). VII (0.5 g.) in 5 cc. 6N HCl heated 0.5 hr. at 80° gave VIII, decomposing above 205°. K (4 g.) under 60 cc. Et₂O treated during 1 hr. with 13.8 g. absolute EtOH, warmed 3-4 hrs. on the water bath, treated at 0-5° with stirring with 14.6 g. III, the mixture treated after 10 min. during 0.5 hr. with 18.9 g. N-benzoyl-2-pyrrolidone in 27 cc. dry dioxane, diluted after 1 hr. with 150 cc. Et₂O, and filtered after 12 hrs., the residue dried in vacuo (23 g.), added with stirring to 40 cc. H₂O, 15 cc. HCl, and 30 cc. CHCl₃, the CHCl₃ phase evaporated, the residual oil dissolved at 90° with stirring during 10 min. in 40 cc. 6N HCl, and the hot solution filtered and cooled gave 2 g. VIII, needles, decomposing above 205° with sintering; the mother liquor gave 5.6 g. HO₂CCONH(CH₂)₃CO₂H, m. 163-4° (decomposition) (H₂O or Me₂CO). VIII (20.4 mg.) in 10 cc. H₂O treated with 15 cc. 1% 2,4-(O₂N)₂C₆H₃NHNH₂ in 2N HCl gave the 2,4-dinitrophenylhydrazone of VIII, m. 221° (decomposition). K (20 g.), a few crystals of iodine and a small amount of Hg₂Cl₂ in 50 cc. absolute C₆H₆ treated with 40 cc. absolute EtOH in portions, the mixture diluted with 30 cc. EtOH in 150 cc. C₆H₆, warmed slightly, diluted further with 300 cc. C₆H₆, treated with 43 g. II and 73 g. III, refluxed 18 hrs. with stirring, and treated with 80 cc. 6N HCl, the hot C₆H₆ layer decanted, the aqueous phase extracted with C₆H₆, and the combined C₆H₆ solutions worked up yielded 80% I, m. 148°. I (370 mg.) in EtOH hydrogenated at 20°/760 mm. over PtO₂, filtered, and evaporated gave 3-hydroxy-4-carbethoxy-2-piperidone, m. 121-2° (C₆H₆). I (5.3 g.) and 80 cc. 6N HCl refluxed 6 min. (in larger runs 20 min.) and evaporated at 35°/12 mm., and the residue refrigerated several hrs., filtered, washed with cold HCl, and dried yielded IV, m. 113° (HCl-AcOH-Et₂O). VIII (1.03 g.) and 35 cc. 6N HCl refluxed 1 hr. and evaporated at 35°/16 mm., the residue dissolved in H₂O and chromatographed on Dowex 50-X-8 (H form), and the fractions from 207-358 cc. evaporated gave 0.7 g. IV, m. 113° (decomposition). IV (48.7 mg.) hydrogenated 3 hrs. at 21°/755 mm. over PtO₂, filtered, treated with Ag₂O and then H₂S, refiltered, and evaporated, and the residue and 48 mg. picric acid dissolved in hot glacial AcOH and diluted with Et₂O gave the picrate of V, m. 134-5°. I (12.5 g.) and 200 cc. 6N HCl refluxed 7 min., concentrated at 40°/25 mm. to 30 cc., diluted with 120 cc. H₂O, hydrogenated 5 hrs. at 25°/1 atm. over 270 mg. PtO₂, filtered, placed on Amberlite IR-4B, washed with 1.3 l. H₂O, and eluted gave 5.51 g. pure V. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0HPLC of Formula: 30727-21-0).

Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 30727-21-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Acyl-lactone rearrangement. XXIII. Syntheses of cyclic amino acids by the reaction principle of the acyl-lactone rearrangement was written by Buechel, Karl Heinz;Korte, Friedhelm. And the article was included in Chemische Berichte in 1962.Name: Ethyl 2,3-dioxopiperidine-4-carboxylate The following contents are mentioned in the article:

3-Ethoxalyl-2-pyrrolidones and 3-ethoxalyl-2-piperidones were converted by heating with decarboxylation and rearrangement and by subsequent catalytic hydrogenation to DL-hygrinic acid (I), DL-proline (II), and DL-N-methylpipecolinic acid (III), resp., in high yields. N-Methyl-2-pyrrolidone and (CO₂Et)₂ (IV) were condensed with coarsely cut and with powd. K to yield 56 and 60-65%, resp., 3-ethoxalyl-N-methyl-2-pyrrolidone (V). V (1 g.) in 25 cc. concentrated HCl refluxed 20 hrs., concentrated in vacuo, diluted with 20 cc. H₂O, treated with 1 g. 2,4-(O₂N)₂C₆H₃NHNH₂ in 170 cc. 2N HCl, and kept several days gave the 2,4-dinitrophenylhydrazone of MeNH(CH₂)₃-COCO₂H, m. 183-4° (2N HCl). V (10 g.) in 60 cc. concentrated HCl refluxed 20 hrs. until the maximum at 285 mμ had disappeared, concentrated to 50 cc., cooled, filtered, from 0.1-0.3 g. V, diluted with H₂O, hydrogenated over 0.5 g. PtO₂, filtered, and evaporated, and the residual I.HCl (9 g.) dissolved in H₂O, passed through weakly basic Duolite A 7, and evaporated gave I, m. 174-5° (EtOH-Et₂O); I.HCl m. 183-5° (EtOH-Et₂O). 2-Pyrrolidone heated with excess Ac₂O gave 95% N-Ac derivative (VI), b₁₂ 109-10°. VI (127 g.) and 204 g. IV in 100 cc. dry Et₂O added dropwise at -5 to 0° to 39.1 g. powd. K and 1 cc. absolute EtOH in 400 cc. dry Et₂O, stirred 8 hrs., added with stirring and cooling to 500 cc. 2N HCl, and extracted with CHCl₃ gave 209 g. (crude) 3-ethoxalyl-N-acetyl-2-pyrrolidone (VII), b_0.05 90-5°, blue-violet with FeCl₃; the higher boiling fractions deposited 3-ethoxalyl-2-pyrrolidone, m. 134-6° (ligroine), blue with FeCl₃. Crude VII (5 g.) and 20 cc. 6N HCl heated 24 hrs. at 60° gave 1.2 g. 3-oxalyl-2-pyrrolidone, m. 208-10° (decomposition). VI (127 g.) and 180 g. IV added dropwise with stirring to 39.1 g. K and 1 cc. absolute EtOH in 400 cc. dry MePh at about 100° and worked up in the usual manner yielded 160 g. (crude) [EtO₂C(CH₂)₃NHCO]₂ (VIII), needles, m. 103-6° (ligroine, b. 80-110°). VIII refluxed with 6N HCl gave [HO₂C-(CH₂)₃NHCO]₂, m. 212°. The brown semisolid residue from the mother liquor from VIII treated in EtOH with C, concentrated, and diluted with petr. ether gave 26 g. 2,3-dioxo-4-carbethoxypiperidine, m. 148° (C₆H₆), ruby-red with FeCl₃. VII (22.7 g.) in concentrated HCl refluxed 1 hr., concentrated to half-volume, diluted with an equal volume H₂O, hydrogenated over 0.5 g. PtO₂, and worked up, and the residual crude II.HCl dissolved in H₂O, passed through Duolite A 7, eluted with 1.5 l. H₂O, and evaporated yielded 9 g. II, m. 214-15°. VII treated in the usual manner with 2,4-(O₂N)₂C₆H₃NH-NH₂ yielded the 2,4-dinitrophenylhydrazone of H₂N(CH₂)₃-COCO₂H, yellow, m. 217-18° (2N HCl). α-Ethoxalyl-N-methyl-2-piperidone (21.3 g.) added to 100 cc. boiling 6N HCl, refluxed about 5 min., concentrated to about 40 cc., diluted with an equal volume H₂O, hydrogenated over 0.5 g. PtO₂, and worked up yielded 17.9 g. III.HCl, m. 195-200°. III.HCl in H₂O treated with Amberlite 4-B and evaporated gave 14.0 g. III, m. 208-10° (EtOH-Et₂O). III treated in the usual manner with 2,4-(O₂N)₂C₆H₃-NHNH₂ gave the 2,4-dinitrophenylhydrazone of MeNH(CH₂)₄-COCO₂H, yellow needles, m. 207° (2N HCl). III (2.9 g.) in MeOH methylated with MeI-Ag₂O yielded DL-homostachydrine (IX), very hygroscopic crystals, m. 207-8° (EtOH-Et₂O); IX.-HCl, m. 211° (EtOH-Et₂O). This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0Name: Ethyl 2,3-dioxopiperidine-4-carboxylate).

Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Name: Ethyl 2,3-dioxopiperidine-4-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem