A robust and recyclable polyurea-encapsulated copper(I) chloride for one-pot ring-opening/Huisgen cycloaddition/CO2 capture in water

Green Chemistry International

Green Chem., 2016, 18,6357-6366
DOI: 10.1039/C6GC01956K, Paper
Yun Chen, Wei-Qiang Zhang, Bin-Xun Yu, Yu-Ming Zhao, Zi-Wei Gao, Ya-Jun Jian, Li-Wen Xu
One-pot ring-opening/Huisgen cycloaddition reactions combined with CO2 capture were carried out successfully in the presence of polyurea-encapsulated CuCl.
A robust and recyclable polyurea-encapsulated copper(I) chloride for one-pot ring-opening/Huisgen cycloaddition/CO2 capture in water
Yun Chen,a Wei-Qiang Zhang,a Bin-Xun Yu,a Yu-Ming Zhao,a Zi-Wei Gao,*a Ya-Jun Jiana and Li-Wen Xu*ab
*Corresponding authors
aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education (MOE) and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. China
E-mail: liwenxu@hznu.edu.cn, zwgao@snnu.edu.cn
bKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou 311121, P. R. China
Green Chem., 2016,18…

View original post 88 more words

Moving along the pyridine ring — amphoteros

A couple of weeks ago, I finished teaching the synthesis of pyridine and its derivatives in my 4th year synthesis class. Whenever I present this material, I can’t help but appreciate the value of N-oxidation. While there are N-oxides of other heterocycles (thiazole N-oxide stands out for its interesting properties), nowhere else do I feel […]

via Moving along the pyridine ring — amphoteros

Acetylcholine Chloride

New Drug Approvals

Acetylcholine Chloride



Molecular Formula: C7H16ClNO2
Molecular Weight: 181.66 g/mol

Acetylcholine chloride is obtained as white or off-white hygroscopic crystals, or as a crystalline powder. The salt is odorless, or nearly odorless, and is a very deliquescent powder. Acetylcholine bromide is obtained as deliquescent crystals, or as a white crystalline powder. The substance is hydrolyzed by hot water and alkali

Image result for acetylcholine chloride

Acetylcholine is an organic chemical that functions in the brain and body of many types of animals, including humans, as a neurotransmitter—a chemical released by nerve cells to send signals to other cells. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic. Substances that interfere with acetylcholine activity are called anticholinergics.

Acetylcholine is the neurotransmitter used…

View original post 590 more words


New Drug Approvals

N,N′-(6,6′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis- (methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide)

Mp: 72−74 °C.

1 H NMR (400 MHz, CDCl3): δ 1.25 (6H, s), 1.29 (18H, s), 3.84−3.90 (4H, m), 4.27−4.31 (2H, m), 6.84−6.87 (3H, t), 6.97−7.00 (2H, dd), 7.09−7.13 (3H, t), 7.43−7.45 (10H, m), 9.0−9.01 (4H, d), 8.43 (2H, br s);

13C NMR (100 MHz, CDCl3): δ 25.88, 30.02, 34.10, 55.01, 61.53, 77.36, 108.43, 111.4, 118.73, 120.4, 124.09, 124.34, 126.67, 127.38, 128.35, 135.30, 138.25, 144.74, 148.62, 150.99, 156.07, 156.71, 160.56;

MS: m/z 1142.2 (M + H);

Elem. Anal: Found: C 59.87, H 5.20, N 12.38; Calcd for C57H60N10O12S2: C 59.99, H 5.30, N 12.27

Abstract Image

A new and efficient synthetic process for the synthesis of an endothelin receptor antagonist, bosentan monohydrate, involves the coupling of ptert-butyl-N-(6-chloro-5-(2-methoxy phenoxy)-2,2′-bipyrimidin-4-yl)benzenesulfonamide (7) with (2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol (14) as a key step. This new process provides desired bosentan monohydrate (1) with better quality and…

View original post 52 more words

Heck–Matsuda Reaction in Flow

Abstract Image

Product 3 was obtained as a mixture of diastereomers (58:42). The NMR data are consistent with literature precedent.20a

Major diastereomer: 1H NMR (300 MHz, CDCl3) δ (ppm) 7.25-7.28 (m, 2H), 7.14-7.17 (m, 2H), 5.14 (dd, 1H, J = 2.5, 5.8 Hz), 4.29 (t, 1H, J = 8.3 Hz), 3.79 (dd, 1H, J = 6.9, 8.4 Hz), 3.54-3.62 (m, 1H), 3.38 (s, 3H), 2.32 (dd, 1H, J = 7.7, 12.9 Hz), 2.04 (ddd, 1H, J = 5.1, 9.3, 13.1 Hz);

Minor diastereomer: 1H NMR (300 MHz, CDCl3) δ 7.25-7.28 (m, 4H), 5.16 (d, 1H, J = 4.4 Hz), 4.17 (t, 1H, J = 8.1 Hz), 3.72 (dd, 1H, J = 8.5, 9.7 Hz), 3.42 (s, 3H), 3.32-3.36 (m, 1H), 2.59 (ddd, 1H, J = 5.5, 10.3, 13.7 Hz), 1.91 (ddd, 1H, J = 2.4, 7.7, 10.2 Hz);

13C NMR (75 MHz, CDCl3) δ (ppm) 141.4, 140.0, 132.4, 132.3, 129.1, 128.7, 128.7, 128.5, 105.7, 105.4, 73.7, 73.0, 54.9, 54.7, 43.6, 42.1, 41.4, 41.1.

(20) (a) Oliveira, C. C.; Angnes, R. A.; Correia, C. R. D. J. Org. Chem. 2013, 78, 4373. (b) Oliveira, C. C.; Pfaltz, A.; Correia, C. R. D. Angew. Chem. Int. Ed. 2015, 54, 14036.

The optimization of a palladium-catalyzed Heck–Matsuda reaction using an optimization algorithm is presented. We modified and implemented the Nelder–Mead method in order to perform constrained optimizations in a multidimensional space. We illustrated the power of our modified algorithm through the optimization of a multivariable reaction involving the arylation of a deactivated olefin with an arenediazonium salt. The great flexibility of our optimization method allows to fine-tune experimental conditions according to three different objective functions: maximum yield, highest throughput, and lowest production cost. The beneficial properties of flow reactors associated with the power of intelligent algorithms for the fine-tuning of experimental parameters allowed the reaction to proceed in astonishingly simple conditions unable to promote the coupling through traditional batch chemistry.


BioAssay Express: models mixing assays & compounds — Cheminformatics 2.0

The latest experimental feature of the BioAssay Express project involves taking all of the curated assays (3500 so far) and their corresponding compounds from PubChem (hundreds of thousands of unique structures) and feeding them all into one giant Bayesian model. Rather than the usual approach of modelling compound ⟹ activity separately for each assay, this approach takes advantage […]

via BioAssay Express: models mixing assays & compounds — Cheminformatics 2.0

Simultaneous rapid reaction workup and catalyst recovery

Green Chemistry International

Simultaneous rapid reaction workup and catalyst recovery

Green Chem., 2016, 18,5769-5772

DOI: 10.1039/C6GC02448C, Communication

Zhichao Lu, Zofia Hetman, Gerald B. Hammond, Bo Xu

By combining reaction work-up and catalyst recovery into a simple filtration procedure we have developed a substantially faster technique for organic synthesis.

By combining reaction work-up and catalyst recovery into a simple filtration procedure we have developed a substantially faster technique for organic synthesis. Our protocol eliminates the time-consuming conventional liquid–liquid extraction and is capable of parallelization and automation. Additionally, it requires only minimal amounts of solvent.

Simultaneous rapid reaction workup and catalyst recovery

Zhichao Lu,a   Zofia Hetman,a   Gerald B. Hammond*a and  Bo Xu*b  

 *Corresponding authors

aDepartment of Chemistry, University of Louisville, Louisville, USA

bCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu…

View original post 329 more words