Substrate selective synthesis of pyrazolo[1,5-a]pyridines through [3 + 2] cycloaddition of N-aminopyridines and β-nitro styrenes

RSC Advances ◽  
2015 ◽  
Vol 5 (53) ◽  
pp. 42961-42964 ◽  
Author(s):  
Chitrakar Ravi ◽  
Darapaneni Chandra Mohan ◽  
N. Naresh Kumar Reddy ◽  
Subbarayappa Adimurthy

Synthesis of 2 or 3-(hetero)aryl pyrazolo[1,5-a]pyridines through [3 + 2] cycloaddition ofN-aminopyridine with β-nitrostyrenes followed byin situdenitration under metal-free and mild conditions are described.

2021 ◽  
Author(s):  
Hassan Seyrani ◽  
Sorour Ramezanpour ◽  
Aref Vaezghaemi ◽  
Farzad Kobarfard

A convenient, transition-metal-free access to a series of unprecedented saccharin substituted 2,5-dihydropyrroles is reported. This approach employs a post-Ugi-Smiles 5-endo-dig Conia-ene cyclization sequence in mild conditions while incorporating a series...


2017 ◽  
Vol 15 (15) ◽  
pp. 3165-3169 ◽  
Author(s):  
Ming-Tao Chen ◽  
Xia You ◽  
Li-Gang Bai ◽  
Qun-Li Luo

Heteroarene N-oxides were successfully converted to heteroarylphosphonates in a very short time under mild conditions through in situ activation with CBrCl3.


Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2311-2315 ◽  
Author(s):  
Gaofeng Feng ◽  
Jing-Yao He ◽  
Qi-Fan Bai ◽  
Chengan Jin

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6H-benzo[c]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed or generated in situ from the corresponding amines with t-BuONO. The process is amenable to gram-sale synthesis of 6H-benzo[c]chromenes, which can be further transformed into both 6H-benzo[c]chromen-6-ones through oxidation or to 6H-benzo[c]chromen-6-amine through sp3 C–H bond amination. The protocol provides an attractive route for the synthesis of a library of 6H-benzo[c]chromes.


Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1071-1075 ◽  
Author(s):  
Vit Lellek ◽  
Cheng-yi Chen ◽  
Wanggui Yang ◽  
Jie Liu ◽  
Xuebao Ji ◽  
...  

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.


2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yongmeng Wu ◽  
Cuibo Liu ◽  
Changhong Wang ◽  
Yifu Yu ◽  
Yanmei Shi ◽  
...  

AbstractElectrocatalytic alkyne semi-hydrogenation to alkenes with water as the hydrogen source using a low-cost noble-metal-free catalyst is highly desirable but challenging because of their over-hydrogenation to undesired alkanes. Here, we propose that an ideal catalyst should have the appropriate binding energy with active atomic hydrogen (H*) from water electrolysis and a weaker adsorption with an alkene, thus promoting alkyne semi-hydrogenation and avoiding over-hydrogenation. So, surface sulfur-doped and -adsorbed low-coordinated copper nanowire sponges are designedly synthesized via in situ electroreduction of copper sulfide and enable electrocatalytic alkyne semi-hydrogenation with over 99% selectivity using water as the hydrogen source, outperforming a copper counterpart without surface sulfur. Sulfur anion-hydrated cation (S2−-K+(H2O)n) networks between the surface adsorbed S2− and K+ in the KOH electrolyte boost the production of active H* from water electrolysis. And the trace doping of sulfur weakens the alkene adsorption, avoiding over-hydrogenation. Our catalyst also shows wide substrate scopes, up to 99% alkenes selectivity, good reducible groups compatibility, and easily synthesized deuterated alkenes, highlighting the promising potential of this method.


Author(s):  
Jingwen Guo ◽  
Lina Zhang ◽  
Xinyue Du ◽  
Liting Zhang ◽  
Yuepiao Cai ◽  
...  
Keyword(s):  

Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...


2021 ◽  
Vol 9 (12) ◽  
pp. 7556-7565
Author(s):  
Guojian Chen ◽  
Yadong Zhang ◽  
Ke Liu ◽  
Xiaoqing Liu ◽  
Lei Wu ◽  
...  

Constructing phenanthroline-based cationic radical porous hybrid polymers as versatile metal-free heterogeneous catalysts for both oxidation of sulfides and CO2 conversion.


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