Chiral oxygen ligands

Computed Properties of C6Cl2N4. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5,6-Dichloropyrazine-2,3-dicarbonitrile, is researched, Molecular C6Cl2N4, CAS is 56413-95-7, about Preparation of magnesium azaphthalocyanines by cyclotetramerization of S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles. Author is Mrkved, Eva H.; Holmaas, Lars T.; Kjsen, Helge; Hvistendahl, Georg.

Four novel S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles were obtained in a multistep synthesis from diaminomaleonitrile. Two of these dicarbonitriles, with Et or benzyl S-substituents, give pure Mg azaphthalocyanines in good yields when reacted with Mg propoxide in PrOH and dioxane. Aromatic S-substituents are less stable during the reaction conditions used for cyclizations, and product mixtures were obtained.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: cis-4-Aminocyclohexane carboxylic acid, is researched, Molecular C7H13NO2, CAS is 3685-23-2, about Synthesis and antitumor activity of nonsymmetric phosphoric acid triamides, the main research direction is phosphoric acid triamide nonsym preparation acute toxicity antitumor activity; amide phosphoric acid nonsym preparation acute toxicity antitumor activity.Recommanded Product: cis-4-Aminocyclohexane carboxylic acid.

R1R2P(O)NHR3 (R1, R2 independently = aziridino, N(CH2CH2Cl)2, NMe2, morpholino or NHCH2CH2OH; R3 = 4-R-substituted cyclohexyl (R = H, cis- and trans-CO2H, cis- and trans-CO2Et)) were prepared and tested for acute toxicity and antitumor activity. All the 12 tested compounds possess a lower antitumor activity as compared to that of the reference drug thiophosphamide. The antitumor activity of nonsym. phosphoric acid triamides is determined for the most part by the nature of amide residues attached at the P atom. The antitumor effect can be varied within a broad range by changing this residue, the maximum antitumor activity being inherent in nonsym. triamides containing the ethylenimine residue.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Soil Biology & Biochemistry called Management induced organic matter differentiation in grassland and arable soil: a study using pyrolysis techniques, Author is Nierop, Klaas G. J.; Pulleman, Mirjam M.; Marinissen, Joke C. Y., which mentions a compound: 616-43-3, SMILESS is CC1=CNC=C1, Molecular C5H7N, Quality Control of 3-Methyl-1H-pyrrole.

Differences in agricultural management and land use lead to differences in soil structure, soil organic matter (SOM) dynamics and composition We investigated the SOM composition at 3 depth layers in a permanent pasture (PP), an organic arable (OA) and a conventional arable (CA) field within one soil series in marine loam deposits in The Netherlands. Both arable fields were in the grass phase of the rotation. The chem. composition of SOM was determined by a combination of conventional pyrolysis-gas chromatog./mass spectrometry (Py-GC/MS) and of thermally-assisted hydrolysis and methylation (THM) with tetramethylammonium hydroxide (TMAH). In PP, SOM was composed of relatively little decomposed, mainly grass-derived material comprising polysaccharides, lignin, aliphatic compounds (extractable lipids, cutin, suberin) and proteins. With depth, plant-derived constituents decreased, whereas microbial and humified material predominated. Both arable soils contained mainly strongly humified plant material and microbially altered proteineous material that showed heterocyclic N-compounds together with alkylbenzenes and phenols upon pyrolysis. With THM, small traces of plant-derived alkanols and cutin/suberin were observed in the arable soils. The upper layers of OA contained little lignin, which can only be derived from the grass vegetation or manure inputs since last plowing (2 yr before), since it was not found in the whole plow layer. Overall SOM composition is therefore hardly affected by organic farming compared to conventional management. The differences in SOM content and composition between the pasture and arable fields can be ascribed to differences in input and depth distribution of fresh organic materials. A difference in phys. protection of easily mineralizable SOM between pasture and arable soils is also likely to contribute.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 3685-23-2, is researched, SMILESS is N[C@H]1CC[C@H](CC1)C(O)=O, Molecular C7H13NO2Journal, Article, Research Support, U.S. Gov’t, Non-P.H.S., Brain Research called Effects of some conformationally restricted GABA analogs on GABA membrane binding and nerve ending transport, Author is Hitzemann, Robert J.; Loh, Horace H., the main research direction is GABA transport brain; receptor GABA brain membrane.Computed Properties of C7H13NO2.

By using a series of aminocyclopentane- and aminocyclohexanecarboxylic acids, as well as some naturally occurring amino acids, it was possible to determine some aspects of the spatial topog. of the GABA [56-12-2] membrane binding and transport sites in the rat brain. The Na-independent GABA binding site had a different spatial topog. than the Na-dependent binding site in that (±)-trans-3-aminocyclopentanecarboxylic acid (I) [19297-28-0] was 7-fold more potent than (±)-cis-3-aminocyclopentanecarboxylic acid (II) [49805-32-5] in inhibiting Na-independent binding, but only 1.6 times more potent in inhibiting Na-dependent binding. The nerve ending GABA transport site was similar to the Na-dependent GABA binding site in that it accommodated both I and II. However, the transport site differed from the binding site in that II was a potent inhibitor of transport but a weak inhibitor of binding. In addition to the differences in spatial characteristics, differences in the subcellular distribution of Na-independent and Na-dependent binding sites were observed The former were found primarily in the nerve ending-mitochondrial fraction, whereas the latter were primarily found in the microsomal fraction.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 56413-95-7, is researched, SMILESS is N#CC1=NC(Cl)=C(Cl)N=C1C#N, Molecular C6Cl2N4Journal, Journal of Heterocyclic Chemistry called Synthesis of pyrido[1′,2′:1,2]imidazo[4,5-b]pyrazines from 2,3-dichloro-5,6-dicyanopyrazine with 2-aminopyridines, Author is Suzuki, Toshinobu; Nagae, Yasushi; Mitsuhashi, Keiryo, the main research direction is chlorodicyanopyrazine cyclocondensation aminopyridine; pyridoimidazopyrazine.Recommanded Product: 5,6-Dichloropyrazine-2,3-dicarbonitrile.

Novel synthesis of the title compounds I (R = H, 6-, 7-, 8-, 9-Me, 8-Cl, 8-Br, 6-PhCH2O) by the facile cyclization between 2,3-dichloro-5,6-dicyanopyrazine and various 2-aminopyridines II under relatively mild conditions is described. The reactivity depended on the basicity of 2-aminopyridines.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of an octadecapeptide and its 18-amide analog corresponding to the first eighteen amino acid residues of corticotropin (ACTH) and their biological activities》. Authors are Otsuka, Hideo; Inouye, Ken; Shinozaki, Fusako; Kanayama, Makoto.The article about the compound:cis-4-Aminocyclohexane carboxylic acidcas:3685-23-2,SMILESS:N[C@H]1CC[C@H](CC1)C(O)=O).Product Details of 3685-23-2. Through the article, more information about this compound (cas:3685-23-2) is conveyed.

The title compound (I) and its 18-amide analog (II) were synthesized. The activities of I, II, H-Gly-Tyr-Ser-Met-Glu-His-Phe-Arg-Try-Gly-Lys-Pro-Val-Gly-Arg-Arg-OH (III) (CA 63, 670f), and H-Gly-Tyr-Ser-Met-Glu-His-Phe-Arg-Try-Gly-Lys-Pro-Val-Gly-Lys-Arg-Arg-NH2 (IV) (CA 63, 16462d) were compared (cf. the table). (BOC = tert-BuO2C and Cbz = PhCH2O2C). Steroidogenic U.S.P. units/mg., Lipolytic minimal effective dose (γ); In vivo, In vitro, Rabbit, Rat; I, 17.07, 9.35, 0.000075, 0.0045; II, 39.6;58.0, 4.7;11.5, 0.000004, 0.0027; III, 0.124, 0.134, 0.00093, 0.021; IV, 2.72; 1.26, 0.00042, 0.0037; Coupling of BOC-Ser-Tyr-Ser-Met-N3 with H-Glu(γ-tert-Bu)-His-Phe-Arg-Try-Gly-OH gave BOC-Ser-Tyr-Ser-Met-Glu(γ-tert-Bu)-His-Phe-Arg-Try-Gly-OH (V), m. 202° (decomposition), [α]24D -13.2° (c 1.0, HCONMe2). Reaction of Cbz-Lys(BOC)-Pro-Val-Gly-Lys(BOC)-N3 with either H-Lys(BOC)-Arg-Arg-OH or its amide gave Cbz-Lys(BOC)-Pro-Val-Gly-Lys(BOC)-Lys(BOC)-Arg-Arg-OH (VI), [α]25.5D -46.1° (c 1.0, 50% AcOH), or its amide (VII), [α]22.5D -43.7° (c 1.75, 50% AcOH). Coupling of N-hydroxysuccinimide ester of V with the hydrogenolyzed VI or VII gave BOC-Ser-Tyr-Ser-Met-Glu(γ-tert-Bu)-His-Phe-Arg-Try-Gly-Lys(BOC)-Pro-Val-Gly-Lys(BOC)-Lys(BOC)-Arg-Arg-OH (VIII) or its amide (IX), resp. VIII was purified on carboxymethyl cellulose columns and treated with 90% F3CCO2H to give I, λ (0.1N NaOH) 281.5 mμ (ε 7030), 288.5 mμ (ε 6820), [α]25D -54.6° (c 0.5, 0.1N AcOH). Similarly, IX gave II, λ (0.1N NaOH) 281.5 mμ (ε 7050), 288.5 mμ (ε 6740), [α]24D -55.8° (c 0.5, 0.1N AcOH). Amino acid analysis of I and II confirmed their structures.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Lee, Bum Hoon; Jaung, Jae Yun; Jeong, Sung Hoon published the article 《Synthesis and dyeing properties of dicyanopyrazine dyes》. Keywords: cyanopyrazine dye preparation use polyamide polyester.They researched the compound: 5,6-Dichloropyrazine-2,3-dicarbonitrile( cas:56413-95-7 ).Category: chiral-oxygen-ligands. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:56413-95-7) here.

Reaction of 2,3-dichloro-5,6-dicyanopyrazine with various Fischer’s base type enamines gave the corresponding 2-chloro-5,6-dicyanopyrazine derivatives The reactive-disperse dyes showed large differences in λmax from solution to solid state resulting from strong intermol. π-π interactions. These dyes have rather small mol. size but have a strong intramol. charge-transfer chromophoric system. The absorption maxima of these compounds were observed at 463∼560 nm. The electronic character of the substituents in the dyes strongly affects their absorption spectra, producing bathochromic shifts depending on both the basicity of the heterocyclic moiety and the enlargement of the π-conjugated system. The dyeability of 2 of the dyes toward polyester and nylon fiber were generally good. Wash, perspiration, and rubbing fastness were excellent, while light fastness was poor, probably due to the oxidation of the enamine moiety.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《New synthesis of serotonin》. Authors are Noland, Wayland E.; Hovden, Robert A..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).HPLC of Formula: 616-43-3. Through the article, more information about this compound (cas:616-43-3) is conveyed.

Dropwise addition of a molar excess of nitroethylene to molten 5-benzyloxyindole at steam bath temperature 1.83 hrs. gave 3-(2-nitroethyl)-5-benzyloxyindole (I), m. 93.5-5.0° (CH2Cl2-ligroine), in 45% yield. Use of excess nitroethylene is desirable since unreacted 5-benzyloxyindole (36%) and 64% I form a eutectic mixture, m. 81-1.5°. Similar reactions of 5-benzyloxyindole with equimolar portions of β-nitrostyrene 6 hrs. and β-methyl-β-nitrostyrene for 22 hrs. gave 72 and 37% yields, resp., of 3-(1-phenyl-2-nitroethyl)-5-benzyloxyindole (II), platelets, m. 117-18° (alc.), and 3-(1-phenyl-2-nitropropyl)-5-benzyloxyindole (III), m. 152-2.5° (alc.). Hydrogenation at 2 atm. over PtO2 of I-III gave in high yields the corresponding tryptamines, isolated as the picrates. I gave 84% yield as reddish orange crystals, m. 231.5-2.0° (decomposition). III gave 94% yield, red crystals, m. 176-6.5° (alc.) and III gave 62% yield, red crystals, m. 213-15°. The tryptamine from I was characterized as the hydrochloride, m. 245-7° (decomposition). Hydrogenation of I at 2 atm. over 10% Pd-C resulted in concomitant reduction of the NO2 group and debenzylation to give 69% serotonin (IV) as the creatinine sulfate hydrate, m. 212-14°. This new synthesis of IV from 5-benzyloxyindole appeared to be higher in over-all yield than most reported methods. It was also simpler than previously described methods.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Identification of two chromogens in the Elson-Morgan determination of hexosamines. A new synthesis of 3-methylpyrrole. Structure of the “”pyrrolenephthalides””》. Authors are Cornforth, J. W.; Firth, M. E..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Recommanded Product: 616-43-3. Through the article, more information about this compound (cas:616-43-3) is conveyed.

The substance producing most of the color with Ehrlich’s reagent in the Elson-Morgan assay of hexosamines is shown to be 2-methylpyrrole (I); 3-acetyl-2-methylpyrrole (II) is also formed. A synthesis of 3-methylpyrrole (III) in 4 steps from CH2:CMeCH2Cl (IV) is described. Infrared spectra indicate that the condensation products of pyrroles with ο-C6H4(CO)2O (V) are benzo[f]pyrrocoline-5,10-diones; several of these are described. D-Glucosamine-HCl (VI) (21.6 g.) in 800 cc. H2O was added to an aqueous solution (2200 ml.) containing 106 g. Na2CO3, 19.6 g. Ac2CH2, and 200 ml. N HCl, the mixture at pH 9.75 in 2 portions heated on steam baths under reflux condensers, heating continued 20 min., the solutions cooled below 30°, combined, distilled at 20 mm., and the receiver cooled, until the distillate gave no color with Ehrlich’s reagent. The distillate (450 ml.) saturated with NaCl, extracted with Et2O, shaken once with 2N NaOH and H2O, the combined aqueous and alk. solutions reëxtd. with Et2O, the extracts evaporated at -10°/30-40 mm., the residue distilled at room temperature and 1 mm. gave 650 mg. I, b766 138-46°. I remained colorless in N at -5° but darkened in air. The infrared spectrum was identical with that of authentic I. The residual liquors after collection of the aqueous distillate combined, heated 45 min., then distilled, the pyrrole precipitated as the Hg complex, the solid suspended in N Na2CO3, and decomposed with H2S gave 40 mg. I. The aqueous reaction mixture from I extracted continuously 24 hrs. with Et2O, and the product distilled at 0.6-0.7 mm. gave a product which sublimed above 100°/0.05 mm., the sublimate suspended in 1:1 Et2O-ligroine, and the solid collected gave 130 mg. II, m. 94-5° (ligroine), ν 1620 cm.-1 in KCl, and 1660 cm.-1 in CCl4. Aminoacetal (3 g.) with 1 ml. H2O added dropwise in the cold to 18 g. HCl, after 5 hrs. at room temperature the solution neutralized to methyl orange, 1.39 g. Ac2CH2 added at once, the pH adjusted to 10, after 24 hrs. at 5° the mixture saturated with salt and extracted with Et2O, the Et2O concentrated, and the residue sublimed below 100°/0.5 mm. and crystallized gave II. II would not form a semicarbazone or 2,4-dinitrophenylhydrazone. Pyrrole-2-aldehyde (5 g.) refluxed 15 min. with 10 g. KOH, 7.5 ml. 90% N2H4.H2O, and 100 ml. O(CH2CH2OH)2, the mixture heated so that I slowly distilled (with some H2O, N2H4, and glycol) (after 4-5 hrs. the condensate was weakly Ehrlich pos.), a little H2O added to the distillate, the lower layer saturated with NaCl, and extracted with Et2O gave 3.65 g. I. 2-Acetylpyrrole (1.5 g.) similarly gave 0.81 g. 2-ethylpyrrole, b20 65°. VI (250 μg.) in 5 ml. H2O heated 25 min. in a stoppered flask immersed in a bath at 95-100° with 5 ml. of a solution of 1 ml. Ac2CH2 in 50 ml. 0.5N Na2CO3, two 1-ml. samples (O1,O2) were withdrawn, the remainder concentrated at 20 mm., the thawed distillate diluted with 8 ml. H2O and a 1-ml. portion (D) taken. The residue also diluted to 8 ml. with H2O and two 1-ml. samples (R1,R2) drawn. A solution (P) of 2.45 μg. I in H2O was prepared by suitable dilutions Samples O1, D, R1, and P were treated with 5 ml. alc., followed after mixing by 0.5 ml. Ehrlich reagent. Samples O2 and R2 received 0.5 ml. of 1:1 alc.-acid. The solutions were kept 1-2 hrs. at room temperature Solutions O2 and R2 showed no significant difference from B when examined at 530 and 540 mμ. Solutions O1, D, R1 and P were measured with O2 as control. The following results were obtained (λ in mμ, optical density of O1, D, R1, and P given): 500, 0.089, 0.051, 0.038, 0.144; 510, 0.120, 0.070, 0.050, 0.203; 520, 0.154, 0.098, 0.060, 0.269; 530, 0.179, 0.121, 0.056, 0.323; 535, 0.183, 0.132, 0.050, -; 540, 0.186, 0.139, 0.040, 0.375; 544, -, 0.141, -, 0.386; 545, 0.185, 0.141, 0.030, 0.386; 550, 0.176, 0.138, 0.025, 0.377; 560, 0.125, 0.100, 0.020, 0.287. Two solutions of II (200 μg. and 10 μg.) in H2O were treated with alc. and Ehrlich reagent. After 1 hr. the stronger solution was pale pink and after 1 week it had become deep purple and the weaker one was pale pink. HC(OEt)3 (90 ml.) and 35 g. Mg heated at 60°, 2 ml. IV added, followed by a little MeI, cooling being required to keep the temperature below 70°, 49.5 ml. more IV added at such a rate as to maintain a temperature of 60°, next day the flask cooled, saturated NH4Cl added dropwise until the mixture became solid, the cake collected, and the filtrate evaporated gave 45 g. 3-methyl-3-butenal diethyl acetal (VII), b18-19 58-60°, b745 162°, n21D 1.4155. VII (13.2 g.) in 20 ml. Et2O treated gradually with 85 ml. ethereal M perphthalic acid, allowed to warm, and kept below 30° by occasional cooling, the next day the phthalic acid removed, and the filtrate extracted with aqueous NaHCO3 gave 10.9 g. 3,4-epoxy-3-methylbutanal diethyl acetal (VIII), b17 83-4°. VIII (3 g.) and 20 ml. MeOHNH3 kept 24 hrs. at 37° and distilled gave 1.95 g. 4-amino-3-hydroxy-3-methylbutanal diethyl acetal (IX), b17 130°, purple color with Ehrlich reagent. Aqueous NH3, either at 100° for 3.5 hrs., or at room temperature 48 hrs. also opened the epoxide ring; the best yield of IX was 65%. IX (1.5 g.) distilled with a solution of 4.5 g. citric acid in 400 ml. H2O until the Ehrlich test became weak and III was isolated from the distillate as for I, giving 200 mg. III, b. 142-3°, darkened rapidly in the air. III (38%) was obtained by dissolving IX in H2O and 3 g. citric acid and distilling the whole in stream until 400 ml. distillate had collected; a Hg complex of III was formed when IV was kept 2 days at 40° with 450 mg. NH4OAc, 2.5 ml. 0.5N AcOH, and 900 mg. HgCl2 with occasional shaking. The following general procedure for preparing benzopyrrocolinediones was developed. The pyrrole (x g.) and 10x g. V mixed with 15x g. AcOH in a tube and when sealed heated 2 hrs. at 180-90°, the product refluxed with H2O, the black residue extracted with hot alc., the alc. filtrate taken to dryness, the residue treated with C6H6, filtered, and the filtrate after concentration chromatographed on Al2O3 gave the crystalline benzopyrrocolinedione. I (600 mg.) gave 98 mg. 3-methylbenzo[f]pyrrocoline-5,10-dione, needles, m. 173-4° (ligroine), ν 1708 and 1655 cm.-1. A mixture of 1- and 2-methylbenzo[f]pyrrocoline-5,10-diones (57 mg.) was obtained from 200 mg. III. Recrystallization from alc. gave 18 mg. of one isomer, m. 223°. The mother liquors and washings from the 1st recrystallization evaporated and the residue crystallized gave 13 mg. of the other isomer, m. 169-70°. Both isomerides showed ν 1708 and 1655 cm.-1 in KCl. 2-Ethylpyrrole (364 mg.) gave 43 mg. 1-ethylbenzo[f]pyrrocoline-5,10-dione, m. 114°, after sublimation in vacuo and crystallization from MeOH. Condensation of 2,4-dimethylpyrrylmagnesium bromide [from 6.4 g. 2,4-dimethylpyrrole (IXa)] and 5 g. V in Et2O gave a solid by filtration after decomposition of the mixture with ice and CO2; the aqueous filtrate extracted with Et2O and acidified and the precipitates combined and crystallized gave 7.2 g. 2-(ο-carboxybenzoyl)-3,5-dimethylpyrrole (X), m. 195-6.5° (decomposition) (MeOH-H2O). X on warming with Ehrlich reagent developed a cherry red color. X (100 mg.) refluxed 1.5 hrs. with 2 ml. H2O and 5 drops NH4OH gave 27.5 mg. 1,3-dimethylbenzo[f]pyrrocoline-5,10-dione (XI), m. 181-3° (alc.), ν 1705, 1650 cm.-1 KCl, λ 378, 318, 267, 237 mμ, log ε 3.67, 3.71, 4.28, and 4.42, resp. XI was also obtained on heating IXa and V by the standard procedure. XI (52.5 mg.) heated 1 hr. with 2 ml. 2N NaOH gave X.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Maksheeed, Saad; Ibrahim, Fadi; Samuel, Jacob; Helliwell, Madeleine; Warren, John E.; Bezzu, C. Grazia; McKeown, Neil B. published the article 《Clathrate formation from octaazaphthalocyanines possessing bulky phenoxyl substituents: a new cubic crystal containing solvent-filled, nanoscale voids》. Keywords: octaazaphthalocyanine derivative ligand preparation nickel zinc complex; crystal structure octaazaphthalocyanine derivative ligand nickel zinc complex; clathrate formation zinc octaazaphthalocyanine derivative complex solvent.They researched the compound: 5,6-Dichloropyrazine-2,3-dicarbonitrile( cas:56413-95-7 ).Safety of 5,6-Dichloropyrazine-2,3-dicarbonitrile. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:56413-95-7) here.

The synthesis of octaazaphthalocyanine (AzaPc) derivatives, with bulky phenoxyl substituents placed at eight peripheral positions and containing either H+, Ni2+ or Zn2+ ions in their central cavity, is described. The required precursors, derivatives of pyrazine-2,3-dicarbonitrile, were prepared using a nucleophilic aromatic substitution reaction between 2,6-diisopropylphenol or 2,6-diphenylphenol and 5,6-dichloropyrazine-2,3-dicarbonitrile. Anal. of the resulting AzaPcs by UV/Visible and 1H NMR spectroscopy confirms that steric isolation of the AzaPc cores was enforced both in solution and in the solid state. X-ray diffraction studies of single crystals of the AzaPcs reveal that solvent inclusion takes place in each case. Of particular significance is the finding that the Zn derivative of 2,3,9,10,16,17,23,24-octa-(2,6-diisopropylphenoxy)octaazaphthalocyanine provides nanoporous cubic crystals, containing massive (8 nm3) solvent-filled voids, similar to those of the analogous phthalocyanine derivative Exchange of the included solvent within the voids can be readily achieved by using a number of alternative solvents including H2O. Based on the observed loading of included H2O, the internal volume of this nanoporous cubic crystal appears to be more hydrophilic than its phthalocyanine counterpart.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate