Tag: M.W=400-450

Tan, Derek S. published the artcileStereoselective Synthesis of over Two Million Compounds Having Structural Features Both Reminiscent of Natural Products and Compatible with Miniaturized Cell-Based Assays, Synthetic Route of 101-29-1, the publication is Journal of the American Chemical Society (1998), 120(33), 8565-8566, database is CAplus.

A combinatorial library of 2.18 million octahydrobenzoisoxazoles I (R = 2-I, 3-I, 4-I, 2-R⁴CC, 3-R⁴CC, 4-R⁴CC; R¹ = alkyl, cycloalkyl, arylalkyl; R² = alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl; R³ = NH₂, CH₂CONH₂, (CH₂)₅CONH₂; R⁴ = alkyl, aryl, arylalkyl) has been generated to give a set rigid, stereochem. defined, and structurally diverse mols. The libraries are prepared in six steps from either enantiomer of oxacycloheptane II by linking to a solid support with one of three linkers, esterification and dipolar cycloaddition with arylmethyl glycine nitrones, Sonogashira coupling of the product iodoaryl derivatives with alkynes, lactone cleavage with amines, acylation of the free alcs. with acids and acyl coupling reagents, and photochem. cleavage from the resin. Sublibraries of I were prepared to test the reactivity of alkynes, amines, and acids in the preparative sequence towards I and the purity of the products generated. Libraries generated by this sequence are spatially separated and encoded, allowing for controlled release of libraries into solution and for cell-based testing of the libraries.

Journal of the American Chemical Society published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C4H10OS, Synthetic Route of 101-29-1.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Dohrn, M. published the artcile[Haloderivatives of] pyridine[carboxylic acids], Recommanded Product: 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, the publication is Justus Liebigs Annalen der Chemie (1932), 284-302, database is CAplus.

3,5-Diiodochelidamic acid (I) [chloride, m. 149°; Me, m. 173°, Et (II), m. 169°, and benzyl, m. 200° (decomposition), esters] and Me₂SO₄ in aqueous KOH at 35° give 3,5-diiodo-N-methylchelidamic acid (III), m. 174° (decomposition) (Me ester, m. 194-5% while the Ag salt of II and Mel in xylene afford the Et ester, m. 100-1°, of 3,5-diiodo O-methylchelidamic (3,5-diiodo-4-methoxypyridine-2,6-dicarboxylic) acid, decomposes 176°. 3,5-Diiodo-4-ethoxy-, m. 174° (decomposition) (Me ester, m. 131°), -propoxy-, m. 156° (decomposition) (Me ester, m. 89°), -butoxy-, m. 145° (decomposition) (Me ester, m. 82°), and benzyloxy-, m. 167° (decomposition) (Me ester, m. 120°), -pyridine-2,6-dicarboxylic acids are prepared similarly. III heated at 170° gives 3,5-diiodo-N-methyl-4-pyridone, M. 214-5°, also prepared from 3,5-diiodo-4-pyridone (IV), m. 321° (decomposition), and Me₂SO₄ in aqueous KOH; IV is obtained from 4-pyridone and ICl in dilute HCl and by hydrolysis of its N-Ac derivative, m. 245° (decomposition) [from I and boiling AC₂O]. I and IV with ClSO₃H give the corresponding N-sulfo derivatives, m. 210° (decomposition) and 183° (decomposition), resp., hydrolyzed by H₂O to H₂SO₄ and I and IV. 3,5-Diiodo-4-pyridone-N-acetic acid, m. 240° (decomposition), is prepared from IV and CH₂ClCO₂H. 4-Pyridone-2-carboxylic acid (V) and I in aqueous KOH give the 3,5-di-I derivative, decomposes 250° [N-Me, m. 159° (decomposition), and NCH₂CO₂H, m. 223° (decomposition), derivatives]; 2-pyridone-6-carboxylic acid similarly affords the 3,5-di-I derivative, decomposes 272° [N-Me derivative, m. 194° (decomposition)], also formed by iodination of 2-pyridone-5,6-dicarboxylic acid. 3,5-Dichloro-, m. above 300° (N-Me derivative, m. 166°), and 3,5-dibromo-, m. above 300° [N-Me derivative, m. 170° (decomposition)], -4-pyridone-2-carboxylic acids are obtained by halogenation of V. Et 3,5-dichlorochelidamate, m. 96°, and PCl5, give the Et ester, m. 35°, of 3,4,5-trichloropyridine-2,6-dicarboxylic acid, decomposes 150°. 4-Chloro-, m. 232° (decomposition) (Et ester, m. 111°), and 4-bromo-, m. 186° (decomposition) (Et ester, m. 98-9°), -3,5-diiodopyridine-2,6-dicarboxylic acids are prepared from II and PCl5 + POCl₃ and PBr₅, resp. The Et ester of 3,4,5-tri-bromopyridine-2,6-dicarboxylic acid (m. 180° (decomposition)) m. 67°. 3,4,5-Trichloropyridine, m. 76-7°, from 3,5-dichloro-4-pyridone, PCl₅, and POCl₃, at 125°, with EtOH-KHS gives 3,5-dichloro-4-thiolpyridine, m. 188°, oxidized by alk. KMnO₄ to 3,5-dichloro-pyridine-4-sulfonic acid, m. above 300°. 4-Chloro-3,5-dibromo-, m. 98°, and 4-chloro 3,5-diiodo-, m. 175°, -pyridines are similarly converted by way of 3,5-dibromo-, m. 222°, and 3,5-diiodo-, m. 206° (decomposition), -4-thiolpyridines into 3,5-dibromo- (VI) and 3,5-diiodo- (VII), decompose 308°, -pyridine-4-sulfonic acids. 3,5-Dibromo- and 3,5-diiodopyridine-2-sulfonic acids, both decompose above 300°, are prepared similarly. VI and aqueous NH₃ (d. 0.91) at 130° give 3,5-dibromo-4-aminopyridine, m. 169-70°;3,5-dibromo-4-anilino-, m. 167°, and -4-o-carboxyanilino-, m. 252° (as Et ester, m. 105-6°), -pyridines are formed with PhNH₂ and o-NH₂C₆H₄.CO₂Et, resp. When an aqueous solution of VI is heated, 3,5,3′,5′-tetrabromo-N-4′-pyridyl-4-pyridone, m. above 300°, and SO₂ are formed. 3,5,3′,5′-Tetraiodo-N-4′ -pyridyl-4-pyridone, decomposes above 300°, is obtained similarly from VII.

Justus Liebigs Annalen der Chemie published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Recommanded Product: 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bojarska-Dahlig, H. N. published the artcileDerivatives of pyridine N-oxide. XV. Synthesis and reactivity of N-[4-oxo-1(H)-pyridyl]oxyacetic acid, Category: iodides-buliding-blocks, the publication is Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1958), 331-9, database is CAplus.

cf. C.A. 51, 15516a. 4-Hydroxypyridine N-oxide (I) in alk. medium with ClCH₂CO₂H yielded almost 60% title compound (II), decomposed with CH₂N₂ to give 4-MeOC₆H₄N, CO₂, and HCHO. I (3.33 g.) in 20 ml. H₂O containing 3.12 g. NaOH kept 5 hrs. at 90-5° with 4.23 g. ClCH₂CO₂H, the mixture adjusted to pH 3 with acid, kept overnight at 0°, and crystallized (H₂O) yielded 57% II, C₇H₇NO₄, m. 164-5°. II (0.4 g.) in 90% alc. hydrogenated with Pd-C (4 mg. PdCl₂ reduced in 25 ml. 96% alc. in the presence of 36 mg. C) and the filtered solution evaporated gave 4-oxo-1 (H)-pyridone (III); nitrate, m. 194-5° (decomposition). II (0.845 g.) heated 5 hrs. with 2 g. Ba(OH)₂ in 10 ml. H₂O, the mixture treated with dilute H₂SO₄, the filtered solution (A) concentrated, and the residue treated with fuming HNO₃ at 0° yielded 63% III nitrate. A acidified with AcOH and treated with concentrated aqueous CaCl₂ gave (OHCCO₂)₂Ca. II (0.1 g.) boiled 2 min. with 3 ml. 2N NaOH and the solution (1 ml.) acidified with dilute H₂SO₄ and treated with 1 drop 0.1% aqueous indole and 1 ml. H₂SO₄ gave a red color. The solution (1 ml.) acidified with AcOH and treated with a few drops of egg white and 1 ml. H₂SO₄ gave a pos. Adamkiewicz reaction for OHCCO₂H (IV). (CO₂H)₂, produced by partial conversion of IV, was detected in the rest of the liquid. II (0.845 g.) and 0.84 g. CH₂N₂ in 240 ml. Et₂O kept 20 hrs. at room temperature, the Et₂O evaporated, the residue treated with 10 ml. alc. picric acid, and the product recrystallized (alc.) yielded 52% 4-MeOC₅H₄N.C₆H₃N₃O₇, m. 173-4°. The presence of CO₂ and HCHO was demonstrated but no trace of IV was found. I. (1.65 g.) in 50 ml. H₂O containing 2.4 g. Na₂CO₃ at 95-100° treated dropwise with vigorous stirring with 7.8 g. iodine in 24 ml. H₂O containing 7.8 g. KI, the mixture kept 1 hr. at 95-100°, the free iodine removed with KHSO₃, the solution adjusted to pH 2 with concentrated HCl, the mixture kept 10 hrs., filtered, the crude product (3.52 g.) boiled with 4% aqueous HCl, and the residue washed with H₂O gave 3,5-diiodo-4-hydroxypyridine N-oxide (V), m. 340-3° (decomposition), also obtained in 13% yield by stirring 1.65 g. I and 3.2 g. NaOH in 50 ml. H₂O at 95-100° with addition of 7.62 g. iodine in 40 min., heating the mixture 1 hr. at 95-100°, repeatedly precipitating with concentrated HCl, and dissolving the precipitate in concentrated NaOH, or by treating 1 g. I in 5 ml. 20% HCl 2 hrs. at 95-100° with HgICl in 8 ml. 20% HCl, diluting the mixture with 80 ml. H₂O, heating 2 hrs. at 95-100°, treating with NaHSO₃, and filtering. V (3.63 g.) in 25 ml. H₂O containing 1.44 g. NaOH heated 5 hrs. at 90-5° at pH 8 with 1.88 g. ClCH₂CO₂H, the mixture adjusted to pH 2 with concentrated HCl, kept 12 hrs. at room temperature, filtered, the precipitate (3.85 g.) boiled with 100 ml. H₂O, filtered from 0.94 g. V, the filtrate evaporated, and the residue (2.88 g.) recrystallized (H₂O) gave authentic N-(3,5-diiodo-4-oxo-1(H)-pyridyl)acetic acid (VI), m. 250.5-1.5°, methylated with CH₂N₂ in Et₂O to VI Me ester (VII), m. 198-8.5° (50% MeOH), not yielding a picrate with picric acid in alc. V (1 g.) heated 5.5 hrs. on a steam bath in 15 ml. 10% NaOH and the cooled solution acidified below pH 2 with concentrated HCl gave 87% unchanged V. The ultraviolet absorptions of 10^-4M solutions in 50% alc. were determined and tabulated [compound, and λ_maximum and λ_min. in mμ (log ε) given]: II, 268, 222 (4.1, 2.85); 4-benzyloxypyridine N-oxide (cf. Shaw, C.A. 43, 2997e), 269, 231 (4.3, 3.05); N-benzyloxy-4-oxo-1(H)pyridine, 268, 230 (4.3, 2.8); VI, 238 and 285, 257 (4.1 and 3.95, 3.65); VII, 238 and 285, 257 (4.0 and 3.95, 3.65); N-(4-oxo-1 (H)-pyridyl)acetic acid, 202 and 261, 221 (4.1 and 4.2, 3.1); Et N-(4-oxo-1 (H)-pyridyl)acetate, 204 and 260, 221 (4.1 and 4.25, 2.8).

Recueil des Travaux Chimiques des Pays-Bas et de la Belgique published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Category: iodides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Dingjan, H. A. published the artcileThe Guerbet reaction applied to diodone, Recommanded Product: 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, the publication is Mikrochimica Acta (1978), 2(5-6), 395-402, database is CAplus.

In the 1st step of the Guerbet test, applied to diodone acid (I), the nitration products II and III are formed. In the 2nd (reduction) step with Zn-HCl, products IV and V are formed.

Mikrochimica Acta published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Recommanded Product: 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Baker, Wilson published the artcilePreparation of iodine-containing x-ray contrast substances. I. 3,5-Diiodo-4-pyridone-N-acetic acid (“Perabrodil”), Application of 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, the publication is Journal of the Society of Chemical Industry, London (1943), 189-91, database is CAplus.

The synthesis of 3,5-diiodo-4-pyridone-1-acetic acid (I), m. 247°, used for the visulization of the urinary tract, was effected by the following steps: pyridine, containing 2% AlCl₃, in (CHCl₂)₂ was treated with 1 mol. Br at room temperature for 48 hrs., thus forming 4-pyridylpyridinium bromide-HBr, the aqueous solution of which, after freeing from (CHCl₂)₂, was hydrolyzed at 150° for 8 hrs., giving rise to a solution of pyridine-HBr and 4(1)-pyridone (II). This mixture was iodinated directly in aqueous NaOH by boiling with iodine and by making the solution alternately acid with concentrated HCl and alk. with 20% NaOH, 6 times during the course of 1 hr. The mechanism of the iodination is obscure; the product is 3,5-diiodo-4-pyridone (III) obtained, on final acidification and treatment with SO₂, as a cream-colored precipitate Moist III (250 g.) in warm aqueous NaOH (48 g. in 460 ml. H₂O) was heated with 60 g. CH₂ClCO₂H for 1 hr. and then treated with powd. NaCl. The separated Na salt of I yielded 107 g. I on acidification. I is polymorphous, crystallizing from H₂O in hexagonal plates, needles, or fernlike crystals.

Journal of the Society of Chemical Industry, London published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Application of 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Musante, Carlo published the artcileSome salts and derivatives of 3,5-diiodo-4(1H)-pyridone-1-acetic acid, Synthetic Route of 101-29-1, the publication is Gazzetta Chimica Italiana (1948), 873-80, database is CAplus.

The work was prompted by the growing importance of derivatives of 3,5-diiodo-4(1H)-pyridone-1-acetic acid (I) in radiol. HC:CI.CO.CI:CH.NH (II) was purified by dissolving in a min. of N NaOH, heating at 100°, and repptg. by a current of CO₂. ClCH₂CONEt₂ (III) (4.5 g.), added slowly to 10.5 g. pure II in N NaOH, allowed to stand several hrs. (frequent agitation), and the precipitate purified by EtOH, yields 8.6 g. (62%) N,N-diethyl-3,5-diiodo-4(1H)-pyridone-1-acetamide, m. 231°. Pure HC:CBr.CO.CBr:CH.NH (IV) was prepared by allowing 5.56 g. pyridone in 40 cc. AcOH and 9.3 g. Br to stand 5 h., diluting with water, dissolving the precipitate in N NaOH, and repptg. by CO₂. III (4 g.), added slowly to 5 g. IV, allowed to stand several hrs., and the precipitate purified by EtOH, yields approx. 5 g. 3,5-dibromo-N,N-diethyl-4(1H)-pyridoneacetamide, m. 224-5°. II (4.4 g.) in 20 cc. N NaOH agitated with 2.5 cc. Me₂SO₄, heated to 100°, allowed to stand 30 min., and the precipitate purified by water, yields 4 g. HC:CI.CO.CI:CH.NMe (V). Aqueous KMnO₄ (400 cc. of 1%) added slowly to aqueous V (1 g. in 180 cc.), and the mixture steam-distilled, yields CHI₃; the residue, filtered and concentrated, yields a solution containing an iodide (indicated by acidification with H₂SO₄ and addition of CHCl₃ and Cl water). In contrast to this, II is not oxidized by KMnO₄ under the same conditions. However, boiling II and aqueous KMnO₄ several hrs. yield a little iodide and (CO₂H)₂. I (2 g.) and 15 cc. SOCl₂, refluxed 2 h. (the solution turns red, then colorless), distilled, and the residue taken up in Et₂O, dissolved in aqueous NaOH, and reprecipitated by CO₂, yield II. Salts of I were prepared from alc. I and aqueous solutions of salts of the metals concerned. They are probably of normal electrovalent structure, of low solubility in water and organic solvents, and melt at high temperatures, with decomposition Salts: Ag, from AgNO₃ (100% yield), m. 297°, turns brown in light; Pb, from acidic Pb(OAc)₂, m. approx. 300°; Cd, from Cd(OAc)₂, lustrous, m. 286°; mercuric, from Hg(OAc)₂, m. 253°; cupric, from Cu(OAc)₂, blue-green, m. 257°; Zn, from Zn(OAc)₂, m. 285°; Co, from Co(NO₃)₂ buffered by NaOAc, rose color, turns brown at 200°, violet at 240°, blackish at 270°, and m. 295°; Ni, from Ni(OAc)₂, light green (no m.p. given); ferric, from FeCl₃, ocher-yellow, turns almost black 270°, m. 290°; La, from boiling aqueous LaCl₃, turns brown approx. 270°, decompose around 300°, solubility in water 3.33 × 10^-4 g.-mol./l. at 20°; Pr, from PrCl₃, turns brown around 280-5°, decompose around 300°; Nd, from boiling aqueous (PhS)₃Nd, begins to decompose 285°, decompose completely 300°; Sm, from boiling aqueous (PhS)₃Sm, decompose around 300°; Gd, from boiling aqueous (PhSO₃)₃Gd, decompose around 300°, solubility in water 3.33 × 10^-4 g.-mol./l. at 20°. Pb 3,5-dibromo-4(1H)-pyridone-1-acetate, (C₇H₄O₃NBr₂)₂Pb, from Pb(OAc)₂ and HC:CBr.CO.CBr:CH.NCH₂CO₂H, no m.p. given.

Gazzetta Chimica Italiana published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Synthetic Route of 101-29-1.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Ates, Oznur published the artcileChromatographic study of some iodinated organic compounds. II, Application of 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, the publication is Journal of Faculty of Pharmacy of Istanbul University (1968), 4(1), 36-49, database is CAplus.

Iodipamide, iodipamide methyglucamate, 3,5-diiodo-4-pyridone-N-acetic acid and its methylglucamine salt, Me and Et 3,5-diiodo-4-pyridone-N-acetate, and iodochlorhydroxyquin were determined by paper and thin-layer chromatog., and the iodinated compounds were visualized by the ceric sulfate-arsenious acid reagent. In order to avoid the fading of the spots, some aromatic amines were used as a second spray on the chromatograms previously treated with the ceric sulfate-arsenious acid reagent. Most of these drugs gave 1 spot on paper and a silica gel layer. Iodochlor-hydroxyquin gave 2 spots on silica gel, and 3 spots on plates covered with polyamide.

Journal of Faculty of Pharmacy of Istanbul University published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C7H5I2NO3, Application of 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Shanazarov, K. S. published the artcileSynthesis of hydroxyalkyl esters of pelvirinic acid [3,5-diiodo-4-oxo-1(4H)-pyridineacetic acid], HPLC of Formula: 101-29-1, the publication is Khimiko-Farmatsevticheskii Zhurnal (1969), 3(4), 21-2, database is CAplus.

The title acid (I) was esterified with ethylene glycol and with 1,2-propylene glycol by a method to produce, resp., potential x-ray-contrasting substances β-hydroxyethyl 3,5-diiodo-4-pyridine-N-acetate (II) and β-hydroxypropyl 3,5-diiodo-4-pyridone-N-acetate (III) resp. Thus, a mixture of 30 g. I, 60 ml. ethylene glycol, 150 ml. C6H6, and 5 g. cationite KU-2 was boiled 2 hrs. with intense stirring until H2O ceased to collect in the H2O-separator. The mixture was cooled, 200 ml. Me2CO added and worked up to yield 84.8% II, m. 190.5-91°. Similarly prepared was 82.4% III m. 170-2° (EtOH).

Khimiko-Farmatsevticheskii Zhurnal published new progress about 101-29-1. 101-29-1 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Iodide,Carboxylic acid,Ketone, name is 2-(3,5-Diiodo-4-oxopyridin-1(4H)-yl)acetic acid, and the molecular formula is C9H6FNO, HPLC of Formula: 101-29-1.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com