scholarly journals Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

2014 ◽  
Vol 10 ◽  
pp. 2338-2344 ◽  
Author(s):  
András Demjén ◽  
Márió Gyuris ◽  
János Wölfling ◽  
László G Puskás ◽  
Iván Kanizsai

5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2857-2869
Author(s):  
Demyd S. Milokhov ◽  
Vasyl Y. Hys ◽  
Olesya B. Volovenko ◽  
Irina S. Konovalova ◽  
Svitlana V. Shishkina ◽  
...  

Synthetic approach to fused azasultams with 1,2,4-thiadi­azepine framework via base promoted protocols has been developed. 1H-Azole-2-carboxylates and N-(chloromethyl)-N-methylmethanesulfonamide were used as ambiphilic building blocks in the one-pot and two-step reaction sequences. Chemical behavior of the obtained azasultams in reactions with amines, hydrazine, DMFDMA, and NaBH4 was investigated. An enamino ketone derived from an azasultam was exploited in the synthesis of new pyrazole and pyrimidine heterocycles.


SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 1-3 ◽  
Author(s):  
Reuben James ◽  
Sharon Herlugson ◽  
Sami Varjosaari ◽  
Vladislav Skrypai ◽  
Zainab Shakeel ◽  
...  

A one-pot, direct reductive acetylation of aldehydes was achieved under mild conditions using 1-hydrosilatrane as a safe and easily accessible catalyst. Described herein is a facile synthesis that produces acylated primary alcohols that can serve as valuable building blocks for organic synthesis. The method has good functional group tolerance and works for a range of aryl aldehydes, with the notable exception of electron-rich arenes. A library of esters was isolated by flash chromatography in yields as high as 92%.


2008 ◽  
Vol 23 (10) ◽  
pp. 2796-2803 ◽  
Author(s):  
Jingbo Li ◽  
Wenbo Bu ◽  
Limin Guo ◽  
Zhenxing Chen ◽  
Feng Chen ◽  
...  

A facile one-pot synthetic approach, using oleic acid and oleylamine as composite stabilizers combined with high-temperature treatment in 1-octadecene, has been developed for the preparation of monodisperse and uniform lanthanum phosphate and europium-doped lanthanum phosphate nanocrystals. In particular, with the present synthetic approach, the size of the resulting nanocrystals could be tuned precisely and continuously from 3.5 to 6.5 nm by seed-mediated epitaxial growth. The as-obtained uniform nanocrystals with hydrophobic surfaces, which show efficient photoluminescence, could be easily dispersed in nonpolar solvents. More importantly, these nanocrystals can also be easily modified to water-dispersed ones with hydrophilic surfaces for potential use in in vitro imaging in bioanalysis. In addition, a synthetic mechanism for these monodisperse nanocrystals is presented and discussed.


2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers via a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.<br>


Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.


Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4415
Author(s):  
Sergey A. Usachev ◽  
Diana I. Nigamatova ◽  
Daria K. Mysik ◽  
Nikita A. Naumov ◽  
Dmitrii L. Obydennov ◽  
...  

A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their 5-bromo derivatives. Conditions of chemoselective enediones bromination were found and the key intermediates of the cyclization of bromo-derivatives to 4-pyrones were characterized. Synthetic application of the prepared 4-pyrones has been demonstrated for the construction of biologically important CF3-bearing azaheterocycles, such as pyrazoles, pyridones, and triazoles.


Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 72-83
Author(s):  
Oksana M. Shavrina ◽  
Lyudmyla V. Bezgubenko ◽  
Andrii V. Bezdudny ◽  
Petro P. Onys’ko ◽  
Yuliya V. Rassukana

A convenient synthetic approach to previously unknown NH-iminophosphonates bearing 2-, 3-, and 4-pyridyldifluoromethyl groups at the imine carbon atom was developed. The synthetic potential of these novel building blocks was demonstrated by their conversion into highly functionalized acyclic and heterocyclic aminophosphonates and phosphonic acids combining in their structure biorelevant aminophosphonic fragment, difluoromethyl group, and pyridyl, piperidyl, thiazolidin-4-one, or thiazidinan-4-one heterocyclic moieties in a single molecular platform.


Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1214
Author(s):  
Sergey N. Podyachev ◽  
Rustem R. Zairov ◽  
Asiya R. Mustafina

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.


2021 ◽  
Vol 143 (7) ◽  
pp. 2716-2721
Author(s):  
Jun Zhu ◽  
Yi Han ◽  
Yong Ni ◽  
Guangwu Li ◽  
Jishan Wu

Synlett ◽  
2005 ◽  
pp. 212-216 ◽  
Author(s):  
Frank Schweizer ◽  
Marlin Penner ◽  
David Taylor ◽  
Danielle Desautels ◽  
Kirk Marat

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