Day: April 1, 2022

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 FeCl3-catalyzed selective acylation of amines with 1,3-diketones via C-C bond cleavage, published in 2015-06-03, which mentions a compound: 18362-64-6, mainly applied to amine diketone acylation carbon bond cleavage iron catalyst; amide preparation, Reference of 2,6-Dimethyl-3,5-heptanedione.

We describe a novel FeCl3 catalyzed selective acylation of amines involving the C-C bond cleavage of simple 1,3-diketones. The process proceeds efficiently under a neat condition to give structurally diverse amides. Notably, the acylation process displays high selectivity toward amines over hydroxyl functionality. Traditionally difficult aromatic amines and sterically demanding disubstituted amines can engage in the process with high efficiency.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Aminopyrrole-2-carboxamide( cas:159326-69-9 ) is researched.Product Details of 159326-69-9.Chen, Yanhong; Xiang, Haoyue; Tan, Cun; Xie, Yuyuan; Yang, Chunhao published the article 《A tandem copper (II)-promoted synthesis of 2-substituted pyrrolo[2,1-f][1,2,4] triazin-4(3H)-ones》 about this compound( cas:159326-69-9 ) in Tetrahedron. Keywords: aldehyde aminopyrroleamide annulation cupric chloride catalyst; acetal aminopyrroleamide annulation cupric chloride catalyst; pyrrolotriazinone preparation. Let’s learn more about this compound (cas:159326-69-9).

Annulation of 1-amino-1H-pyrrole-2-amides with various substituted benzaldehydes, heteroaryl aldehydes, alkyl aldehydes or even acetals, promoted by cupric chloride, to synthesize 2-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones was carried out. This approach provides a useful method for constructing the privileged structure in medicinal chem. Electron-donating groups on both partners could accelerate the reaction.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Reference of 2,5-Diphenyloxazole. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2,5-Diphenyloxazole, is researched, Molecular C15H11NO, CAS is 92-71-7, about Long-range exciton diffusion in molecular non-fullerene acceptors. Author is Firdaus, Yuliar; Le Corre, Vincent M.; Karuthedath, Safakath; Liu, Wenlan; Markina, Anastasia; Huang, Wentao; Chattopadhyay, Shirsopratim; Nahid, Masrur Morshed; Nugraha, Mohamad I.; Lin, Yuanbao; Seitkhan, Akmaral; Basu, Aniruddha; Zhang, Weimin; McCulloch, Iain; Ade, Harald; Labram, John; Laquai, Frederic; Andrienko, Denis; Koster, L. Jan Anton; Anthopoulos, Thomas D..

The short exciton diffusion length associated with most classical organic semiconductors used in organic photovoltaics (5-20 nm) imposes severe limits on the maximum size of the donor and acceptor domains within the photoactive layer of the cell. Identifying materials that are able to transport excitons over longer distances can help advancing our understanding and lead to solar cells with higher efficiency. Here, we measure the exciton diffusion length in a wide range of nonfullerene acceptor mols. using two different exptl. techniques based on photocurrent and ultrafast spectroscopy measurements. The acceptors exhibit balanced ambipolar charge transport and surprisingly long exciton diffusion lengths in the range of 20 to 47 nm. With the aid of quantum-chem. calculations, we are able to rationalize the exciton dynamics and draw basic chem. design rules, particularly on the importance of the end-group substituent on the crystal packing of nonfullerene acceptors.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Category: thiazole. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Bis[2-(1-isoquinolinyl-N)phenyl-C](2,4-pentanedionato-O2,O4)iridium(III), is researched, Molecular C35H27N2O2Ir, CAS is 435294-03-4, about Imidazolyl-Phenylcarbazole-Based Host Materials and Their Use for Co-host Designs in Phosphorescent OLEDs. Author is Yi, Rong-Huei; Lei, Ya-Chun; Tseng, Yeh-Hsiang; Lin, Yi-Fan; Cheng, Yen-Chia; Fang, Yu-Chuan; Ho, Cheng-Yung; Tsai, Wei-Wen; Chang, Chih-Hao; Lu, Chin-Wei.

In recent years, owing to the demand for high-efficiency phosphorescent organic light-emitting devices (PhOLEDs), many studies were conducted on the development of bipolar host materials. Imidazolyl-phenylcarbazole-based host materials, i. e., i.m.-CzP, i.m.-CzPCz, i.m.-CzPCMe3, and i.m.-OCzP, were synthesized to obtain high-efficiency green and red-emitting PhOLEDs. With i.m.-OCzP as the host, satisfactory peak efficiencies of 22.2 (77.0 cd A-1 and 93.1 lm W-1) and 14.1% (9.0 cd A-1 and 10.1 lm W-1) could be obtained, resp. To further improve the performance of the devices, an electron transport material, bis-4,6-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PyMPM) was selected to construct a co-hosted system. The efficiency of i.m.-OCzP combined with B3PyMPM forming co-hosts could also achieve high values of 23.0 (80.0 cd A-1 and 98.8 lm W-1) and 16.5% (10.2 cd A-1 and 13.4 lm W-1) for green and red PhOLEDs, resp. These results exhibited that the proposed bipolar hosts have great flexibility in adjusting the carrier balance of EML in OLEDs, demonstrating their ingenious design and high potential.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Recommanded Product: 92-71-7. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2,5-Diphenyloxazole, is researched, Molecular C15H11NO, CAS is 92-71-7, about Thiocarbamate-directed Cp*Co(III)-Catalyzed Olefinic C-H Amidation: Facile Access to Enamines with High (Z)-Selectivity. Author is Liang, Ya-Ru; Si, Xiao-Ju; Zhang, He; Yang, Dandan; Niu, Jun-Long; Song, Mao-Ping.

A thiocarbamate-directed Cp*Co(III)-catalyzed C-H oxidative amidation of olefins is achieved to synthesize a series of enamines. The key feature of this protocol is the use of earth-abundant cobalt as catalyst and thiocarbamate as directing group, which provides an efficient and simple manner to synthesize enamines in good yields with high (Z)-selectivity. This reaction proceeds smoothly under very mild conditions (rt and air), and a wide range of functionalized alkenes, as well as dioxazolones, were compatible with the standard reaction conditions.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Name: 2-Chloro-5-methylpyridine-3,4-diamine. 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: 2-Chloro-5-methylpyridine-3,4-diamine, is researched, Molecular C6H8ClN3, CAS is 18232-91-2, about Pyridotriazoles and pyridoimidazoles. II. 4,5-Diamino-3-picoline and 3,4-diamino-2,6-lutidine derivatives.

A mixture of 3-methyl-4-aminopyridine in 120 ml. concentrated H2SO4 (d. 1.84) was treated portionwise, at 0°, with 48 ml. HNO3 (d. 1.52) and the mixture kept 1 hr. at room temperature, poured into 300 g. crushed ice, and neutralized with concentrated ammonia to pH 7 to give 32 g. 3-methyl-4-nitraminopyridine (I), m. 212° (H2O). When heated 5 hrs. at 50° and worked up as above, 30 g. I afforded 17.5 g. 3-methyl-4-amino-5-nitropyridine (II), m. 193° (H2O). Reduction of 3 g. II in 100 ml. AcOH with 6 g. powd. Fe, 45 min. at reflux temperature, followed by treatment with a few drops of aqueous HgCl2 and 3 g. Zn dust, neutralization with concentrated KOH, and extraction with Et2O gave 2 g. 3-methyl-4,5-diaminopyridine (III), m. 149° (C6H6-alc.); picrate m. 198°. A solution of 3 g. III in 25 ml. H2O and 1 ml. concentrated H2SO4 was diazotized at 0° with 2.8 g. NaNO2 in 20 ml. H2O and the mixture kept 1 hr. at room temperature, concentrated to the half its original volume, and neutralized with KHCO3 to give 2.4 g. 3-methyl-4,5-pyridotriazole (IV, X = H), m. 260° (H2O). When refluxed 6 hrs., concentrated in vacuo, diluted with 10 ml. H2O, neutralized with KHCO3 to pH 7, then evaporated to dryness, and extracted with absolute alc., a solution of 2 g. III and 4 ml. 100% freshly distilled HCO2H afforded 0.8 g. 3-methyl-4,5-pyridoimidazole (V, X = H), m. 255°. Similarly prepared were the following (compound, m.p., and % yield given): 2,4-dimethyl-4-nitraminopyridine, 206° (decomposition), 93.5; 2,6-dimethyl-3-nitro-4-aminopyridine, 126°, 47.5-78.8; 2,6-dimethyl-3,4-pyridotriazole (VI), 267°, 70; 2,6-dimethyl-3,4-pyridoimidazole (VII), 208°, 56; 3-methyl-6-chloro-4,5-pyridotriazole (IV, X = Cl) (VIII), above 320°, 72. Reduction of 3 g. II with 48 g. SnCl2 in 15 ml. concentrated HCl gave 4 g. 3-methyl-4,5-diamino-6-chloropyridine (IX), m. 157° (H2O). A solution of 1.5 g. IX and 3 ml. hydrazine hydrate in 25 ml. absolute alc. refluxed 3 hrs. afforded 1 g. 3-methyl-6-hydrazino-4,5-pyridotriazole (IV, X = NHNH2), m. 265° (H2O). IX (2 g.) in 4 ml. 100% HCO2H refluxed 6 hrs. and worked up as above gave 1.4 g. 3-methyl-6-hydroxy-4,5-pyridoimidazole (V, X = OH) (X), m. >320°. Heating 2 g. X in 10 ml. POCl3 3 hrs. on a steam bath afforded 1.4 g. 3-methyl-6-chloro-4,5-pyridoimidazole (V, X = Cl) (XI), m. 256° (H2O). When refluxed with hydrazine hydrate 2 g. XI yielded 63% 3-methyl-6-hydrazino-4,5-pyridoimidazole (V, X = NHNH2), m. 220°. Reduction of 2 g. 2,6-dimethyl-3-nitro-4-aminopyridine in 50 ml. hot AcOH with 4 g. Sn led to 1.1 g. 2,6-dimethyl-3,4-diaminopyridine, m. 181° (C6H6); picrate m. 215°.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Recommanded Product: 92-71-7. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2,5-Diphenyloxazole, is researched, Molecular C15H11NO, CAS is 92-71-7, about Catalytic C-H/C-F Coupling of Azoles and Acyl Fluorides. Author is Ogiwara, Yohei; Iino, Yurika; Sakai, Norio.

A method for the palladium/copper-catalyzed direct acylation of azoles with acyl fluorides is described. This study reports the first examples of acyl fluorides being used as acylation reagents in transition-metal-catalyzed aromatic C-H bond functionalization reactions. Depending on the reaction temperature, decarbonylative coupling may also occur. Mechanistic studies suggest that the cleavage of the aromatic C-H bond, promoted by a copper-phosphine species, is not the rate-limiting step of this acylation.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Tang, Guanghui; Liu, Lihong; Wang, Xueying; Pan, Zhengying published the article 《Discovery of 7H-pyrrolo[2,3-d]pyrimidine derivatives as selective covalent irreversible inhibitors of interleukin-2-inducible T-cell kinase (Itk)》. Keywords: pyrrolo pyrimidine derivative preparation Itk kinase inhibitor cancer; 7H-pyrrolo[2,3-d]pyrimidine; Covalent inhibitor; Itk; Selectivity.They researched the compound: Boc-D-Prolinol( cas:83435-58-9 ).Synthetic Route of C10H19NO3. 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:83435-58-9) here.

Interleukin-2-inducible T-cell kinase (Itk) plays an important role in multiple signal transduction pathways in T and mast cells, and is a potential drug target for treating inflammatory diseases, autoimmune diseases, and T cell leukemia/lymphoma. Herein, we describe the discovery of a series of covalent Itk inhibitors based on the 7H-pyrrolo[2,3-d]pyrimidine scaffold. Placing an appropriate substitution group at a hydration site of the ATP binding pocket of Itk and using a saturated heterocyclic ring as a linker to the reactive group were crucial for selectivity. The optimized compound 9 showed potent activity against Itk, excellent selectivity for Itk over Btk and other structurally related kinases, inhibition of phospholipase C-γ1 (PLC-γ1) phosphorylation in cells, and anti-proliferative effects against multiple T leukemia/lymphoma cell lines. Compound 9 can serve as a valuable compound for further determination of functions of Itk.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

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.Shi, Xinzhe; Soule, Jean-Francois; Doucet, Henri researched the compound: 2,5-Diphenyloxazole( cas:92-71-7 ).SDS of cas: 92-71-7.They published the article 《Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts》 about this compound( cas:92-71-7 ) in Advanced Synthesis & Catalysis. Keywords: arylated oxazole regioselective preparation; oxazole aryl bromide arylation palladium catalyst. We’ll tell you more about this compound (cas:92-71-7).

Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole were reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles I [R = H, 4-ClC6H4, 1-naphthyl, etc.; R1 = H, 4-O2NC6H4, 4-pyridyl, etc.] in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system was consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurred via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C-H bond arylation afforded 2,5-diaryloxazoles with two different aryl groups. Also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C-H bond functionalization steps. The Ru-catalyzed C-H arylation of the aryl unit of 2-aryloxazoles was also described.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2,6-Dimethyl-3,5-heptanedione( cas:18362-64-6 ) is researched.Electric Literature of C9H16O2.Tai, Akira; Kikukawa, Tadasi; Sugimura, Takasi; Inoue, Yoshihisa; Osawa, Tsutomu published the article 《Asymmetrically modified Raney nickel catalyst (MRNi). Preparation of highly active new catalyst and its applications》 about this compound( cas:18362-64-6 ) in Shokubai. Keywords: modified Raney nickel asym hydrogenation catalyst. Let’s learn more about this compound (cas:18362-64-6).

Tartaric acid-NaBr-modified Raney nickel catalyst was prepared from ultrasonicated Raney nickel catalyst. This catalyst (TA-NaBr-MRNi-U) showed high hydrogenation activity in the enantiodifferentiating hydrogenation of Me acetoacetate and its homologs, acetylacetone, and 2,6-dimethyl-3,5-heptanedione. From the hydrogenation products, optically pure 3-hydroxybutanic acid and its homologs, 2,4-pentanediol, and 2,6-dimethyl-3,5-heptanediol, were obtained in excellent yield.

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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica