Day: March 30, 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Investigations on the isomerization of ring-substituted derivatives of 3-nitraminopyridines. I. Chloro-3-nitraminopyridines》. Authors are Czuba, Wladyslaw.The article about the compound:5-Chloropyridin-3-aminecas:22353-34-0,SMILESS:NC1=CC(=CN=C1)Cl).HPLC of Formula: 22353-34-0. Through the article, more information about this compound (cas:22353-34-0) is conveyed.

6-(m. 139°), 2- (m. 100-3°), 5- (m. 146°), and 4-Chloro-3-nitraminopyridine (m. 179°) (all with decomposition) heated to 40° in concentrated H2SO4 underwent isomerization to 6,6′-dichloro- (I) (m. 215-17°, yield 10%) and 6,6′-dichloro-2-nitro- (II) (m. 165°, 9%), 2,2′-dichloro- (III) (m. 237-9°, 26%), 5,5′-dichloro- 3, 3′-azopyridine (IV) (m. 183°, 16%) and 5-chloro-3-hydroxypyridine (m. 158°, 32%), and 4,4′-dichloro-3,3′-azopyridine (V) (m. 164°, 40%), resp. I, III, IV, and V with SnCl2, Sn, or NaSH gave the hydrazopyridines, m. 183-5°, 209°, 128-31°, and 172°, resp., yields 70-91%. Reduction of III yielded 6-chloro-2,3-diamino- and -3-aminopyridine. A new method of preparation of 3-amino-5-chloropyridine (VI) was described. Br (32 g.) dissolved in 25 g. NaOH, 50 ml. H2O, and 250 g. ice, 25.5 g. 5-chloronicotinic acid amide added, the mixture heated 0.5 hr. at 75°, the solution saturated with NaCl, extracted with Et2O, dried (K2CO3), and evaporated gave 83% VI, m. 82° (C6H6 + ligroine).

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

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: 1265884-98-7, is researched, SMILESS is N1(P2OC3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5O2)C7=CC=CC=C7C=CC8=CC=CC=C81, Molecular C34H22NO2PJournal, Article, Research Support, Non-U.S. Gov’t, Angewandte Chemie, International Edition called Rhodium-catalyzed asymmetric arylative cyclization of meso-1,6-dienynes leading to enantioenriched cis-hydrobenzofurans, Author is He, Zhi-Tao; Tian, Bing; Fukui, Yuki; Tong, Xiaofeng; Tian, Ping; Lin, Guo-Qiang, the main research direction is hydrobenzofuran enantioselective preparation; dienyne arylboronic acid tandem arylation cyclization rhodium catalyst.Quality Control of 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine.

A tandem rhodium-catalyzed asym. arylative cyclization of cyclohexadienone-containing meso-1,6-dienynes is developed. A series of optically pure cis-hydrobenzofurans were obtained with high to excellent yields (80-99%) and excellent enantioselectivities (95-99% ee). The utility of this method was demonstrated by transforming the cyclization products to chiral frameworks of some natural products.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine(SMILESS: N1(P2OC3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5O2)C7=CC=CC=C7C=CC8=CC=CC=C81,cas:1265884-98-7) is researched.Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde. The article 《Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Bronsted Acid Catalysis》 in relation to this compound, is published in Angewandte Chemie, International Edition. Let’s take a look at the latest research on this compound (cas:1265884-98-7).

The combination of a transition-metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcs. The desired β-naphthalenones, bearing an all-carbon quaternary center, were obtained in good yields with high chemo- and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo- and enantioselectivities relative to single-catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β-naphthalenone enantiomers by simply employing opposite enantiomeric ligands.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Sulfide analogues of flupirtine and retigabine with nanomolar KV7.2/KV7.3 channel opening activity, published in 2019, which mentions a compound: 4360-63-8, mainly applied to flupirtine retigabine potassium channel; KCNQ; KV7; flupirtine; retigabine; sulfides, Electric Literature of C4H7BrO2.

The potassium channel openers flupirtine and retigabine have proven to be valuable analgesics or antiepileptics. Their recent withdrawal due to occasional hepatotoxicity and tissue discoloration, resp., leaves a therapeutic niche unfilled. Metabolic oxidation of both drugs gives rise to the formation of electrophilic quinones. These elusive, highly reactive metabolites may induce liver injury in the case of flupirtine and blue tissue discoloration after prolonged intake of retigabine. We examined which structural features can be altered to avoid the detrimental oxidation of the aromatic ring and shift oxidation toward the formation of more benign metabolites. Structure-activity relationship studies were performed to evaluate the KV7.2/3 channel opening activity of 45 derivatives Sulfide analogs were identified that are devoid of the risk of quinone formation, but possess potent KV7.2/3 opening activity. For example, flupirtine analog 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50=1.4 nM), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Category: dioxole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Biomimetic Enantioselective Total Synthesis of (-)-Robustanoids A and B and Analogues. Author is Liu, Zhan-Jiang; Huang, Pei-Qiang.

We report a step-economical, enantioselective total synthesis of (-)-robustanoid B, I (R = MeO), and (-)-robustanoid A, I (R = OH), and four novel natural product-like compounds Our strategy relied on our biosynthetic hypothesis and on a novel complexity generation methodol., namely, the one-pot hydroxylative double cyclization reaction. The latter consists of a modified 3,3-dimethyldioxirane-triggered epoxidation-epoxide-ring-opening cyclization reaction cascade and Trost’s regioselectivity umpolung methodol. (“”anti-Michael addition””).

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Formula: C11H13OP. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Research and development of phospha sugar anti-cancer agents with anti-leukemic activity. Author is Yamashita, Junko; Suyama, Takuya; Asai, Kazuhide; Yamada, Manabu; Niimi, Taishi; Fujie, Michio; Nakamura, Satoki; Ohnishi, Kazunori; Yamashita, Mitsuji.

We have synthesized three deoxybromophospha sugar analogs, 4-bromo-3-methyl-1-phenyl-2-phospholene 1-oxide (MBMPP (2)), 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (DBMPP (3)), the 2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide (TBMPP (4)), by the reaction of 3-methyl-1-phenyl-2-phospholene 1-oxide (1b) and/or 2 with bromine, and investigated their potentials as anti-leukemic agents against human leukemia cell lines of K562 and U937. Cells’ growth inhibition was determined by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) in vitro assay. All agents showed inhibitory effects on leukemia cell proliferation, indicating that inhibition appeared to be dependent on number of bromine substituent in the heterocyclic structure. Further, the phospha sugar derivatives did not show any inhibitory effects on normal cell proliferation. These agents may facilitate the development of new strategies in mol. targeting anti-leukemic therapy.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Reference of H-Trp-OMe.HCl. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Copper-promoted N-arylation of the indole side chain of tryptophan using triarylbismuthines. Author is Le Roch, Adrien; Chan, Hwai-Chien; Gagnon, Alexandre.

A simple protocol for the regioselective N-arylation of the indole side chain of tryptophan using triarylbismuth reagents as the arylating agent is reported. The reaction is catalyzed by copper(II) acetate, and operates in the presence of triethylamine or pyridine under air at 50°C. This reaction allows the transfer of aryl groups bearing electron neutral, donating or withdrawing substituents at any position of the ring, shows high functional group tolerance, and retains the integrity of the stereogenic center. The protocol was utilized to N-arylate tryptophan-containing di- and tripeptides.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Zhu, Feng; Powell, Wyatt C.; Jing, Ruiheng; Walczak, Maciej A. published the article 《Organometallic AlaM reagents for umpolung peptide diversification》. Keywords: cyclic peptide synthesis solvent effect; alanine carbastannatrane synthon arylation alkylation acylation etherification peptide coupling; cross coupling reaction palladium catalyst zinc insertion; solid phase peptide synthesis macrocyclization chemoselective conjugation palladium.They researched the compound: H-Trp-OMe.HCl( cas:7524-52-9 ).Product Details of 7524-52-9. 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:7524-52-9) here.

Selective modification of peptides and proteins is emerging as a promising strategy to develop novel mechanistic probes and prepare compounds with translational potential. While many methods to perform direct bioconjugation rely on reactions with dehydroalanine, an alternative strategy capitalizing on polarity reversal at the β carbon in amino acids can open access to a new type of diversification reactions characterized by absolute control of regio- and stereoselectivity. Here, we report that alanine carbastannatranes AlaSn can serve as a universal synthon in various C-C and C-heteroatom bond-forming reactions demonstrated in over 50 diverse examples. These reagents are compatible with peptide and protein manipulation techniques and undergo chemoselective conjugation in minutes when promoted by Pd(0). Despite their increased nucleophilicity and propensity to transfer the alkyl group, AlaSn operate at room temperature under buffered conditions (pH 6.5-8.5). We also show that AlaSn can be easily transformed into several canonical L- and D-amino acids in arylation, acylation, and etherification reactions. Furthermore, AlaSn can partake in macrocyclizations exemplified by the synthesis of medium size cyclic peptides with various topologies (7-13 membered macrocycles). Taken together, metalated alanine AlaSn demonstrate unparalleled scope and represent a new type of umpolung reagents suitable for structure-activity relationship studies and peptide diversification.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Product Details of 1265884-98-7. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine.

A regio- and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium-catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane additive and can be switched by changing the nature of the borane. One enantiomer of the ligand is thus sufficient to prepare all possible isomers. The synthetic potential of this method was demonstrated by a short total synthesis of amauromine and its two natural diastereomers.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem