Discovery of 1028-33-7

The article 《Non-human primate SPECT model for determining cerebral perfusion effects of cerebrovasoactive drugs acting via multiple modes of pharmacological action》 also mentions many details about this compound(1028-33-7)Electric Literature of C13H20N4O2, you can pay attention to it, because details determine success or failure

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 Conference, Vascular Dementia, International Congress, 3rd, Prague, Czech Republic, Oct. 23-26, 2003 called Non-human primate SPECT model for determining cerebral perfusion effects of cerebrovasoactive drugs acting via multiple modes of pharmacological action, Author is Oliver, D. W.; Dormehl, I. C.; Louw, W. K. A., which mentions a compound: 1028-33-7, SMILESS is CN1C=NC(N(C(N2CCCCCC)=O)C)=C1C2=O, Molecular C13H20N4O2, Electric Literature of C13H20N4O2.

Increasing clin. and exptl. evidence implicates cerebral hypoperfusion during increased aging and that cerebrovascular insufficiency is a vital component of the neuropathol. progression of dementia. This study describes a baboon Papio ursinus model under anesthesia, for in vivo cerebral blood flow (CBF) determinations, using Single Photon Emission Computed Tomog. (SPECT) following the split-dose method with 99mTc-hexamethylpropylene amine oxime (99mTc-HMPAO) and subsequent pharmacol. intervention studies. Studies were conducted with acetazolamide, pentifylline, nimodipine, sumatriptan and nicotinic acid. Increases in the cerebral perfusion of more than +30% were observed for nimodipine, acetazolamide and the combination of pentifylline and nicotinic acid. Drug interaction studies revealed an attenuation of increased CBF with sumatriptan or acetazolamide in combination with nimodipine. The CBF non-human primate model is therefore useful for the investigation of vasoactive drugs in dementia, acting via various pharmacol. modes of action.

The article 《Non-human primate SPECT model for determining cerebral perfusion effects of cerebrovasoactive drugs acting via multiple modes of pharmacological action》 also mentions many details about this compound(1028-33-7)Electric Literature of C13H20N4O2, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

New downstream synthetic route of 3066-84-0

The article 《Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase》 also mentions many details about this compound(3066-84-0)Computed Properties of C5H4BrN5O, you can pay attention to it, because details determine success or failure

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: 3066-84-0, is researched, SMILESS is NC(N1)=NC(NC(Br)=N2)=C2C1=O, Molecular C5H4BrN5OJournal, Article, Research Support, Non-U.S. Gov’t, Research Support, U.S. Gov’t, Non-P.H.S., Research Support, U.S. Gov’t, P.H.S., Biochimica et Biophysica Acta, Gene Structure and Expression called Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase, Author is Farkas, Walter R.; Jacobson, K. Bruce; Katze, Jon R., the main research direction is tRNA guanine ribosyltransferase specificity reticulocyte; structure activity tRNA guanine ribosyltransferase.Computed Properties of C5H4BrN5O.

A number of compounds, including derivatives of 7-deazaguanine, pteridines, purines, pyrimidines, and antimalarials were tested as inhibitors or substrates of tRNA-guanine ribosyltransferase (EC 2.4.2.29) (I). Virtually all purines and pteridines that were inhibitors or substrates of rabbit reticulocyte I had an amino N atom at the 2-position. In addition, the 9-position and the O atom at the 6-position may be important for recognition by the enzyme. Saturation of the double bond in the cyclopentenediol moiety of queuine (II) reduced the substrate activity and II analogs that lacked the cyclopentenediol moiety, such as 7-deazaguanine and 7-aminomethyl-7-deazaguanine, were relatively poor substrates for I. Adenosine was not an inhibitor of I and neoplanocin A (an adenosine analog in which a cyclopentenediol replaced the ribose moiety) was a poor inhibitor. The incorporation of 7-aminomethyl-7-deazaguanine into the tRNA of L-M cells resulted in a novel chromatog. form of tRNAAsp, indicating that L-M cells cannot modify this queuosone precursor (in Escherichia coli) to queuosine. The specific incorporation of 7-deazaguanine and 8-azaguanine into tRNA by L-M cells also resulted in novel chromatog. forms of tRNAAsp. With intact L-M cells, I-catalyzed insertion into tRNA of II, dihydro-II, 7-aminomethyl-7-deazaguanine, or 7-deazaguanine was irreversible, whereas guanine or 8-azaguanine incorporation was reversible, suggesting that it is the substitution of C-7 for N-7 which prevents the reversible incorporation of II into tRNA.

The article 《Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase》 also mentions many details about this compound(3066-84-0)Computed Properties of C5H4BrN5O, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Some scientific research about 1028-33-7

The article 《Anti-Transcription Factor RNA Aptamers as Potential Therapeutics》 also mentions many details about this compound(1028-33-7)Safety of 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione, you can pay attention to it, because details determine success or failure

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione( cas:1028-33-7 ) is researched.Safety of 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione.Mondragon, Estefania; Maher, Louis James III published the article 《Anti-Transcription Factor RNA Aptamers as Potential Therapeutics》 about this compound( cas:1028-33-7 ) in Nucleic Acid Therapeutics. Keywords: anti transcription factor RNA aptamer review human. Let’s learn more about this compound (cas:1028-33-7).

A review. Transcription factors (TFs) are DNA-binding proteins that play critical roles in regulating gene expression. These proteins control all major cellular processes, including growth, development, and homeostasis. Because of their pivotal role, cells depend on proper TF function. It is, therefore, not surprising that TF deregulation is linked to disease. The therapeutic drug targeting of TFs has been proposed as a frontier in medicine. RNA aptamers make interesting candidates for TF modulation because of their unique characteristics. The products of in vitro selection, aptamers are short nucleic acids (DNA or RNA) that bind their targets with high affinity and specificity. Aptamers can be expressed on demand from transgenes and are intrinsically amenable to recognition by nucleic acid-binding proteins such as TFs. In this study, we review several natural prokaryotic and eukaryotic examples of RNAs that modulate the activity of TFs. These examples include 5S RNA, 6S RNA, 7SK, hepatitis delta virus-RNA (HDV-RNA), neuron restrictive silencer element (NRSE)-RNA, growth arrest-specific 5 (Gas5), steroid receptor RNA activator (SRA), trophoblast STAT utron (TSU), the 3′ untranslated region of caudal mRNA, and heat shock RNA-1 (HSR1). We then review examples of unnatural RNA aptamers selected to inhibit TFs nuclear factor-kappaB (NF-κB), TATA-binding protein (TBP), heat shock factor 1 (HSF1), and runt-related transcription factor 1 (RUNX1). The field of RNA aptamers for DNA-binding proteins continues to show promise.

The article 《Anti-Transcription Factor RNA Aptamers as Potential Therapeutics》 also mentions many details about this compound(1028-33-7)Safety of 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of 1028-33-7

The article 《Rat diaphragm cyclic nucleotide phosphodiesterase. Influence of drugs affecting skeletal muscle contractility》 also mentions many details about this compound(1028-33-7)SDS of cas: 1028-33-7, you can pay attention to it, because details determine success or failure

Klotz, U.; Vapaatalo, H. published an article about the compound: 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione( cas:1028-33-7,SMILESS:CN1C=NC(N(C(N2CCCCCC)=O)C)=C1C2=O ).SDS of cas: 1028-33-7. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1028-33-7) through the article.

Cyclic nucleotide phosphodiesterase (I) [9040-59-9] partly purified from rat diaphragm had a pH optimum of 7.0-8.0 and showed 2 apparent Km values for 3′,5′-cyclic AMP [60-92-4] hydrolysis in the low and high substrate concentration ranges, resp. Various pharmaceuticals inhibited I noncompetitively in the order eupaverin [1163-37-7] ≥ papaverine-HCl [61-25-6] > 1-hexyl-3,7-dimethylxanthine [1028-33-7] > Ro 7-2956 [26772-42-9] > theophylline [58-55-9] > d-tubocurarine chloride [57-94-3] > hydrochlorothiazide [58-93-5]. I was competitively inhibited by N6,2′-O-dibutyryl cyclic AMP [362-74-3] and cyclic GMP [7665-99-8] and noncompetitively by cyclic IMP [3545-76-4]. The mode of action of these drugs might be facilitation of the release of acetylcholine from motor nerve endings via the accumulation of cyclic AMP.

The article 《Rat diaphragm cyclic nucleotide phosphodiesterase. Influence of drugs affecting skeletal muscle contractility》 also mentions many details about this compound(1028-33-7)SDS of cas: 1028-33-7, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

A new synthetic route of 51856-79-2

The article 《3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamides as a New Class of Synthetic Histone Deacetylase Inhibitors. 2. Effect of Pyrrole-C2 and/or -C4 Substitutions on Biological Activity》 also mentions many details about this compound(51856-79-2)Application In Synthesis of Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, you can pay attention to it or contacet with the author([email protected]) to get more information.

Application In Synthesis of Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, is researched, Molecular C8H11NO2, CAS is 51856-79-2, about 3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamides as a New Class of Synthetic Histone Deacetylase Inhibitors. 2. Effect of Pyrrole-C2 and/or -C4 Substitutions on Biological Activity. Author is Mai, Antonello; Massa, Silvio; Cerbara, Ilaria; Valente, Sergio; Ragno, Rino; Bottoni, Patrizia; Scatena, Roberto; Loidl, Peter; Brosch, Gerald.

Previous SAR studies performed on some portions (pyrrole-C4, pyrrole-N1, and hydroxamate group) of 3-(4-benzoyl-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamide (I) highlighted the I-4-phenylacetyl and I-4-cinnamoyl analogs as more potent compounds in inhibiting maize HD2 activity in vitro. In the present paper, we investigated the effect on anti-HD2 activity of chem. substitutions performed on the pyrrole-C2 ethene chains of I and analogs, which were replaced with methylene, ethylene, substituted ethene, and 1,3-butadiene chains. Biol. results clearly indicated the unsubstituted ethene chain as the best structural motif to get the highest HDAC inhibitory activity, the sole exception to this rule being the introduction of the 1,3-butadienyl moiety into the I chem. structure. IC50 values of compounds prepared as I homologues revealed that between benzene and carbonyl groups at the pyrrole-C4 position a hydrocarbon spacer length ranging from two to five methylenes is well accepted by the APHA template, while the introduction of a higher number of methylene units decreased the inhibitory activities of the derivatives Conformationally constrained forms of I analogs, prepared with the aim to obtain some information potentially useful for a future 3D-QSAR study, showed the same or higher HD2 inhibiting activities in comparison with those of the reference drugs. Mol. modeling and docking calculations on the designed compounds performed in parallel with the chem. work fully supported the synthetic effort and gave insights into the binding mode of the more flexible APHA derivatives

The article 《3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamides as a New Class of Synthetic Histone Deacetylase Inhibitors. 2. Effect of Pyrrole-C2 and/or -C4 Substitutions on Biological Activity》 also mentions many details about this compound(51856-79-2)Application In Synthesis of Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, you can pay attention to it or contacet with the author([email protected]) to get more information.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Decrypt The Mystery Of 20028-53-9

The article 《Synthesis of (E)-2,2,2-trifluoro-N-(2-(2-nitrovinyl)phenyl)acetamides》 also mentions many details about this compound(20028-53-9)Synthetic Route of C7H6ClNO, you can pay attention to it, because details determine success or failure

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of (E)-2,2,2-trifluoro-N-(2-(2-nitrovinyl)phenyl)acetamides, published in 2014, which mentions a compound: 20028-53-9, Name is 2-Amino-5-chlorobenzaldehyde, Molecular C7H6ClNO, Synthetic Route of C7H6ClNO.

The synthesis of (E)-2,2,2-trifluoro-N-(2-(2-nitrovinyl)phenyl)acetamides and their applications in the preparation of pharmaceutical intermediates were introduced. Using nitrobenzaldehyde as raw material, (E)-2,2,2-trifluoro-N-(2-(2-nitrovinyl)phenyl)acetamides (I) were synthesized via reduction of nitro group, substitution of amino group and addition reaction. The product structures were characterized by 1H NMR and 13C NMR.

The article 《Synthesis of (E)-2,2,2-trifluoro-N-(2-(2-nitrovinyl)phenyl)acetamides》 also mentions many details about this compound(20028-53-9)Synthetic Route of C7H6ClNO, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The effect of the change of synthetic route on the product 26218-78-0

The article 《Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines by Using Asymmetric Protonation: Method Development and Mechanistic Study》 also mentions many details about this compound(26218-78-0)Computed Properties of C7H6BrNO2, you can pay attention to it, because details determine success or failure

Ashford, Matthew W.; Xu, Chao; Molloy, John J.; Carpenter-Warren, Cameron; Slawin, Alexandra M. Z.; Leach, Andrew G.; Watson, Allan J. B. published an article about the compound: Methyl 6-bromonicotinate( cas:26218-78-0,SMILESS:C1=NC(=CC=C1C(=O)OC)Br ).Computed Properties of C7H6BrNO2. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:26218-78-0) through the article.

A catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines such as I [Ar = Ph, 2-FC6H4, benzo[b]thiophenyl, etc.; Ar1 = quinolin-2-yl, quinoxalin-2-yl, benzo[d]thiazol-2-yl, etc.] is reported. A chiral Bronsted acid promotes aza-Michael addition to fluoroalkenyl heterocycles to give a prochiral enamine intermediate that undergoes asym. protonation upon rearomatization. The reaction accommodates a range of azaheterocycles and nucleophiles, generating C-F stereocenter in high enantioselectivity, and is also amenable to stereogenic C-CF3 bonds. Extensive DFT calculations provided evidence for stereocontrolled proton transfer from catalyst to substrate as rate-determining step, and showed importance of steric interactions from catalyst’s alkyl groups in enforcing high enantioselectivity. Crystal structure data show dominance of noncovalent interactions in core structure conformation, enabling modulation of conformational landscape. Ramachandran-type anal. of conformer distribution and Protein Data Bank mining indicated that benzylic fluorination by this approach has potential to improve potency of several marketed drugs.

The article 《Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines by Using Asymmetric Protonation: Method Development and Mechanistic Study》 also mentions many details about this compound(26218-78-0)Computed Properties of C7H6BrNO2, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Machine Learning in Chemistry about 51856-79-2

The article 《Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes》 also mentions many details about this compound(51856-79-2)Synthetic Route of C8H11NO2, you can pay attention to it, because details determine success or failure

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, is researched, Molecular C8H11NO2, CAS is 51856-79-2, about Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes.Synthetic Route of C8H11NO2.

The reaction of 1,4-naphthoquinone with N-alkylpyrroles gives a mixture of 2-(pyrrol-2-yl)-1,4-naphthoquinones and 2,5-bis(1,4-naphthoquinon-2-yl)pyrroles. The yields and the ratios of these two products depend greatly on the exptl. conditions. The reaction has been extended to 5-hydroxy-1,4-naphthoquinone and 1,2-naphthoquinone. New pyrrolylnaphthoquinone dyes are obtained.

The article 《Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes》 also mentions many details about this compound(51856-79-2)Synthetic Route of C8H11NO2, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The Absolute Best Science Experiment for 20028-53-9

The article 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》 also mentions many details about this compound(20028-53-9)Reference of 2-Amino-5-chlorobenzaldehyde, you can pay attention to it, because details determine success or failure

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》. Authors are Baumgarten, Henry E.; Pedersen, Donald L.; Hunt, Mack W..The article about the compound:2-Amino-5-chlorobenzaldehydecas:20028-53-9,SMILESS:NC1=CC=C(Cl)C=C1C=O).Reference of 2-Amino-5-chlorobenzaldehyde. Through the article, more information about this compound (cas:20028-53-9) is conveyed.

cf. C.A. 50, 8672d. Crude, moist 4,2-Cl(H2N)C6H3CHO (7 g.), 2.9 g. NaNO2, and 75 g. crushed ice slurried in a Waring blender, treated with 9 cc. concentrated HCl and 50 g. crushed ice in 1 portion, blended 5 min. while adding periodically crushed ice, 4.3 cc. MeNO2 in 5 cc. EtOH added slowly with stirring to 5.7 g. KOH in 3.5 l. iced H2O, the solution treated with 3.3 g. NaOAc, the diazonium salt solution added slowly, the mixture allowed to stand 20 min. and filtered, the residue blended about 5-10 min. with 1.3 g. KOH in 50 cc. H2O, the mixture poured into a beaker, allowed to stand 2.5 hrs., and filtered, and the residue dried overnight (1.51 g.) and recrystallized from Me2CO or EtOAc yielded 1.1 g. 7-chloro-3-nitrocinnoline (I), yellow needles, m. 165.6-66° (all m.ps. are corrected). A similar run with a 4-fold larger amount of each reagent was carried out, the resulting yellow solid blended about 10 min. with 5.2 g. KOH in 200 cc. H2O, kept 2.5 hrs., and filtered, the brown residue refluxed 2 hrs. with 300 cc. Me2CO and filtered, and the filtrate treated with C, concentrated to about 75 cc., and cooled, giving 5.5-14.0 g. 5,2-Cl(AcCH:CH)C6H3NHN:CHNO2, yellow-orange needles, m. 234-5° (Me2CO). 5,2-Cl(O2N)C6H3CHO (15.6 g.) in 360 cc. hot EtOH added to 180 g. FeSO4.7H2O in 600 cc. H2O at 90°, the mixture treated slowly during 10 min. with 600 cc. concentrated NH4OH and steam-distilled, the 1st 300-500 cc. distillate discarded, and the following 2 l. distillate cooled to 5°, saturated with NaCl, and filtered yielded 6.5-7.0 g. crude 5,2-Cl(H2N)C6H3CHO (II), m. 73.5-4.5°. Crude moist II (7.0 g.) was converted as described for the preparation of I to 5.1 g. (crude) 6-Cl isomer of I, yellow plates, m. 227-8° (EtOAc). 6-Aminopiperonal (9.0 g.) was converted in the usual manner to nitroformaldehyde 4,5-methylenedioxy-2-formylphenylhydrazone and this to 1.96 g. (crude) 6,7-methylenedioxy-3-nitrocinnoline, cream-colored needles, m. 255-310° (indefinite). 3-Nitrocinnoline (13.8 g.) in 110 cc. AcOH and 55 cc. H2O treated during about 5 min. with 11 g. Fe powder, refluxed 1 hr., poured into 300 g. cold 33% aqueous KOH, kept overnight, and filtered through Celite, the filter cake washed with H2O, suspended in 150 cc. absolute EtOH, heated to boiling, filtered, and again extracted with 150 cc. and 100 cc. absolute EtOH, the combined filtrates evaporated, and the residue recrystallized from 250 cc. C6H6 gave 8.0 g. 3-aminocinnoline (III), m. 165-6°; 2nd crop, 1.1 g. I (3.0 g.) reduced similarly gave 2.2 g. 7-Cl derivative of III, bright yellow plates, m. 202° (decomposition). II (3.0 g.) gave similarly 1.91 g. 6-Cl derivative of III, bright yellow needles, m. 215° (decomposition). ο-O2NC6H4CHO (IV) (10 g.) in 50 cc. absolute MeOH treated with 2 drops concentrated HCl and 0.75 g. CaCl2, the mixture kept 6 days in a desiccator over CaCl2, filtered, neutralized with NaOMe in MeOH, and evaporated, and the oily residue distilled gave 11.4 g. ο-O2NC6H4CH(OMe)2 (V), b27 146-9°, n25D 1.5265. IV (100 g.) in 750 cc. C6H6 and 50 cc. absolute MeOH refluxed 28 hrs. with 2 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removing 500 cc. distillate, neutralized with NaOMe, and worked up in the usual manner yielded 116 g. V. IV (15 g.) in 250 cc. C6H6 and 35 cc. absolute MeOH refluxed 35 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. V. IV (10 g.) in 250 cc. C6H6 and 25 cc. (CH2OH)2 refluxed 30 hrs. with 0.25 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removal of about 150 cc. distillate, basified with NaOMe to litmus, and fractionated gave 10.3 g. ethylene acetal (VI) of IV, pale yellow oil, b0.7 120.7°, n20D 1.5487. IV (15 g.) in 250 cc. C6H6 and 10 cc. (CH2OH)2, refluxed 30 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. VI, b0.7 120°. V (5.0 g.), 100 cc. absolute MeOH, and about 1 g. Raney Ni hydrogenated about 1 hr. at 45 lb., filtered, slurried in a Waring blender with 50 cc. H2O, 3.5 g. NaNO2, and 300 g. crushed ice, treated with 25 cc. 6N HCl, and slurried again 20 min. while adding periodically crushed ice, the mixture added dropwise with stirring during 20 min. to a solution of 3.0 g. MeNO2, 10 cc. EtOH, and 5.7 g. KOH in 400 cc. H2O, and the precipitate recrystallized from 1:3 Me2CO-H2O gave 4.3 g. ο-O2NCH:NNHC6H4CH(OMe)2 (VII), bright orange needles, m. 80-1°. VI (4.3 g.), 50 cc. absolute MeOH, and about 0.5 g. Raney Ni hydrogenated, filtered, diazotized in a blender with 3 g. NaNO2, 100 cc. H2O, 300 g. ice, and 22 cc. 6N HCl, added to a solution of 4 g. MeNO2, 10 cc. EtOH, and 7.5 g. KOH in 400 cc. iced H2O, adjusted with cold 1% HCl to pH 3, stirred 20 min. at 5°, and filtered gave 2.5 g. ethylene acetal (VIII) of ο-O2NCH:NNHC6H4CHO (IX), golden yellow plates, m. 83.6-85° (aqueous Me2CO); the filtrate warmed to room temperature and extracted with Et2O, and the extract evaporated gave 1.8 g. IX, m. 156-8°. VII (0.87 g.) added at 95° to 3 cc. concentrated HCl in 200 cc. H2O in a Waring blender, the solution blended 0.5 hr., cooled to 10°, and extracted with Et2O, and the extract worked up gave 0.66 g. IX, m. 157-8°. VIII (0.65 g.) hydrolyzed similarly with 2 cc. concentrated HCl in 150 cc. hot H2O yielded 0.49 g. IX. IX (2.0 g.) in 300 cc. tetrahydrofuran circulated 18 hrs. at 55° through 6 g. dry Amberlite IRA-400, filtered, and evaporated gave 1.0 g. 3-nitrocinnoline, m. 204-5° (aqueous Me2CO).

The article 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》 also mentions many details about this compound(20028-53-9)Reference of 2-Amino-5-chlorobenzaldehyde, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Research on new synthetic routes about 26218-78-0

The article 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》 also mentions many details about this compound(26218-78-0)Category: tetrahydrofurans, you can pay attention to it, because details determine success or failure

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》. Authors are Lange, Paul P.; Bogdan, Andrew R.; James, Keith.The article about the compound:Methyl 6-bromonicotinatecas:26218-78-0,SMILESS:C1=NC(=CC=C1C(=O)OC)Br).Category: tetrahydrofurans. Through the article, more information about this compound (cas:26218-78-0) is conveyed.

A flow-based synthesis of diversely functionalized indolizines and their aza-analogs is described. These drug-like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2-bromopyridines and alkynes, employing a simple catalyst system together with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base. E.g., in presence of PdCl2(PPh3)2, CuI, and NEt3, followed by addition of DBU in DMF, Sonogashira/cycloisomerization of Me 6-bromonicotinate and N-methyl-N-propargylbenzylamine gave 71% indolizine derivative (I). The use of flow technol. allows a straightforward and rapid access to a variety of novel compounds, and enables linear scale-up from milligram- to gram-scales without a decrease in yield.

The article 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》 also mentions many details about this compound(26218-78-0)Category: tetrahydrofurans, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem