[3+2] Cycloaddition of N-Aminopyridines and Perfluoroalkynylphosphonates: Facile Synthesis of Perfluoroalkylated Pyrazolo[1,5-a]pyridines Containing a Phosphonate Moiety

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3731-3737 ◽  
Author(s):  
Hui Zhang ◽  
Weiguo Cao ◽  
Qi Huang ◽  
Dong He ◽  
Jing Han ◽  
...  

1,3-Zwitterions generated from N-aminopyridines in the presence of base are trapped by perfluoroalkynylphosphonates to yield a variety of perfluoroalkylated pyrazolo[1,5-a]pyridine derivatives bearing a phosphonate group. The salient features of these [3+2] cycloadditions include operational simplicity, good tolerance of functional groups, and good to excellent yields at room temperature.

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2412 ◽  
Author(s):  
Weijia Shi ◽  
Gang Zou

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.


2018 ◽  
Vol 20 (4) ◽  
pp. 827-831 ◽  
Author(s):  
Hao Xie ◽  
Guozheng Li ◽  
Feng Zhang ◽  
Fuhong Xiao ◽  
Guo-Jun Deng

Facile synthesis of 1,2-benzisothiazoles from amidines and elemental sulfur via N–S/C–S bond formation under transition-metal-free conditions has been developed with good tolerance of a broad range of functional groups.


Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 111-115 ◽  
Author(s):  
Banlai Ouyang ◽  
Guanyinsheng Qiu ◽  
Deming Liu ◽  
Kejian Xia ◽  
Yanxia Zheng ◽  
...  

A copper-catalyzed Chan–Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N-arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.


Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 954-958 ◽  
Author(s):  
Fu-Xue Chen ◽  
Pran Karmaker ◽  
Jiashen Qiu ◽  
Di Wu ◽  
Hongquan Yin

A novel and convenient oxidative radical cyclization of N-substituted N-arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K2S2O8 as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.


2016 ◽  
Vol 52 (87) ◽  
pp. 12909-12912 ◽  
Author(s):  
Yunhe Jin ◽  
Haijun Yang ◽  
Hua Fu

An efficient visible-light photoredox decarboxylative coupling of N-(acetoxy)phthalimides with aryl thiols has been developed. The reaction was performed well at room temperature with good tolerance of functional groups. Importantly, the visible-light photoredox decarboxylative arylthiation did not need an added photocatalyst.


2015 ◽  
Vol 12 (1) ◽  
pp. 3910-3918 ◽  
Author(s):  
Dr Remon M Zaki ◽  
Prof Adel M. Kamal El-Dean ◽  
Dr Nermin A Marzouk ◽  
Prof Jehan A Micky ◽  
Mrs Rasha H Ahmed

 Incorporating selenium metal bonded to the pyridine nucleus was achieved by the reaction of selenium metal with 2-chloropyridine carbonitrile 1 in the presence of sodium borohydride as reducing agent. The resulting non isolated selanyl sodium salt was subjected to react with various α-halogenated carbonyl compounds to afford the selenyl pyridine derivatives 3a-f  which compounds 3a-d underwent Thorpe-Ziegler cyclization to give 1-amino-2-substitutedselenolo[2,3-b]pyridine compounds 4a-d, while the other compounds 3e,f failed to be cyclized. Basic hydrolysis of amino selenolo[2,3-b]pyridine carboxylate 4a followed by decarboxylation furnished the corresponding amino selenolopyridine compound 6 which was used as a versatile precursor for synthesis of other heterocyclic compound 7-16. All the newly synthesized compounds were established by elemental and spectral analysis (IR, 1H NMR) in addition to mass spectra for some of them hoping these compounds afforded high biological activity.


2021 ◽  
Author(s):  
Iurii Galadzhun ◽  
Rafal Kulmaczewski ◽  
Namrah Shahid ◽  
Oscar Cespedes ◽  
Mark J Howard ◽  
...  

[Fe(bpp)2][BF4]2 (bpp = 2,6-di{pyrazol-1-yl}pyridine) derivatives bearing a bent geometry of hexadec-1-ynyl or hexadecyl substituents pyrazole are isomorphous, and high-spin at room temperature. However, only the latter compound undergoes an abrupt,...


Nanomaterials ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 623
Author(s):  
Monika Gupta ◽  
Huzein Fahmi Hawari ◽  
Pradeep Kumar ◽  
Zainal Arif Burhanudin ◽  
Nelson Tansu

The demand for carbon dioxide (CO2) gas detection is increasing nowadays. However, its fast detection at room temperature (RT) is a major challenge. Graphene is found to be the most promising sensing material for RT detection, owing to its high surface area and electrical conductivity. In this work, we report a highly edge functionalized chemically synthesized reduced graphene oxide (rGO) thin films to achieve fast sensing response for CO2 gas at room temperature. The high amount of edge functional groups is prominent for the sorption of CO2 molecules. Initially, rGO is synthesized by reduction of GO using ascorbic acid (AA) as a reducing agent. Three different concentrations of rGO are prepared using three AA concentrations (25, 50, and 100 mg) to optimize the material properties such as functional groups and conductivity. Thin films of three different AA reduced rGO suspensions (AArGO25, AArGO50, AArGO100) are developed and later analyzed using standard FTIR, XRD, Raman, XPS, TEM, SEM, and four-point probe measurement techniques. We find that the highest edge functionality is achieved by the AArGO25 sample with a conductivity of ~1389 S/cm. The functionalized AArGO25 gas sensor shows recordable high sensing properties (response and recovery time) with good repeatability for CO2 at room temperature at 500 ppm and 50 ppm. Short response and recovery time of ~26 s and ~10 s, respectively, are achieved for 500 ppm CO2 gas with the sensitivity of ~50 Hz/µg. We believe that a highly functionalized AArGO CO2 gas sensor could be applicable for enhanced oil recovery, industrial and domestic safety applications.


Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1430-1434
Author(s):  
Ming Bian ◽  
Jin-feng Zhou ◽  
Dong-min Tang

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.


Sign in / Sign up

Export Citation Format

Share Document