26409-33-6

Upstream product

• 24903-95-5 nopinone 
• 7089-25-0 2-(4-methoxyphenyl)-3-(dimethylamino)allylidene(dimethyl)ammonium perchlorate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 2457-47-8 3,5-dichloropyridine 
• 625-92-3 3,5-dibromopyridine 
• 1448262-75-6 3,5-bis(tri-n-butylstannyl)pyridine 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 55-21-0 benzamide 
• 768-60-5 4-methoxyphenylacetylen 
• 637-69-4 4-Methoxystyrene 
• 68-12-2 N,N-dimethyl-formamide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 53710-18-2 3,5-diiodopyridine 
• 69519-11-5 2-(4-methoxyphenyl)-[1,3,2]-dioxaborolane 

Downstream Products

• 871096-44-5 3,5-bis-[4-(2-benzyloxy-ethoxy)-phenyl]pyridine 
• 171980-66-8 4,4′-(pyridine-3,5-diyl)diphenol 

Relevant academic research and scientific papers

Base-promoted one-pot synthesis of pyridine derivatives via aromatic alkyne annulation using benzamides as nitrogen source

In the presence of Cs2CO3, the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work.

Two C=C Bond Participation in Annulation to Pyridines Based on DMF as the Nonadjacent N and C Atom Donors

Two C=C bond participation in annulation to pyridines using N,N-dimethylformamide (DMF) as the N1 and C4 synthons has been carried out. In this reaction, DMF contributed one N atom and one C atom to two disconnected positions of pyridine ring, with no need for an additional nitrogen source. Two C=C bonds in two molecules of substituted styrenes offered four carbon atoms in the presence of iodine and persulfate. With the optimized conditions in hand, both symmetric and unsymmetric diaryl-substituted pyridines were obtained in useful yields. On the basis of relevant literature and a series of control experimental results, a possible mechanism was proposed in this work, which may demonstrate how DMF provides both N1 and C4 sources.

Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates

A ligand-free copper catalyzed Suzuki-Miyaura coupling of 3,5-diiodopyridine with aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine A has been successfully synthesized in 60% overall yield.

Discovery of Small-Molecule Inhibitors of Ubiquitin Specific Protease 7 (USP7) Using Integrated NMR and in Silico Techniques

USP7 is a deubiquitinase implicated in destabilizing the tumor suppressor p53, and for this reason it has gained increasing attention as a potential oncology target for small molecule inhibitors. Herein we describe the biophysical, biochemical, and comput

Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes

An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical 3,5-diarylpyridines were synthesized with good to excellent yields. In addition, this method was also utilized for the synthesis of Sch-21418, an anti-inflammatory agent on gram scale.

Cu-Catalyzed concise synthesis of pyridines and 2-(1 H)-pyridones from acetaldehydes and simple nitrogen donors

A highly selective copper-catalyzed concise synthesis of 3,5-diarylpyridine and 2-(1H)-pyridone has been achieved through cascade Chichibabin-type cyclization, C(sp3)-C(sp3) cleavage, and aerobic oxidation. Azide, ceric ammonium nitrate (CAN), and 2-aminopyridine are disclosed as efficient nitrogen donors in this Cu-catalysis using O2 as the oxidant. Water and molecular oxygen were employed as the oxygen source in the case of oxygenation.

Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright

Metal-free synthesis of substituted pyridines from aldehydes and NH4OAc under air

A metal-free and efficient method for the synthesis of substituted pyridines with aldehydes and NH4OAc under mild conditions using air as the oxidant was developed. This oxidative cyclization process involves direct C-H bond functionalization, C-C/C-N bond formation and C-C bond cleavage.

Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions

This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the sameyields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5-and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.

Gyroscope-like platinum and palladium complexes with trans-spanning bis(pyridine) ligands

Pyridines with one or two substituents terminating in vinyl groups are prepared. Intramolecular ring-closing metatheses of trans-MCl2 adducts and hydrogenations supply the title compounds. Williamson ether syntheses using the alcohols HO(CH2)nCH=CH2 (n = 1 (a), 2 (b), 3 (c), 4 (d), 5 (e), 6 (f), 8 (h), 9 (i)) and appropriate halides give the pyridines 2-NC5H4(CH2O(CH 2)nCH=CH2) (1a,b), 3-NC5H 4(CH2O(CH2)nCH=CH2) (2a-e,h,i), and 2,6-NC5H3(CH2O(CH 2)nCH=CH2)2 (4a-d) in 92-45% yields. Reactions of 3,5-NC5H3(COCl)2 and HO(CH 2)nCH=CH2 afford the diesters 3,5-NC 5H3(COO(CH2)nCH=CH2) 2 (5a-f,h, 90-41%). The reaction of 3,5-NC5H 3(4-C6H4OH)2, Br(CH 2)5CH=CH2, and Cs2CO3 yields 3,5-NC5H3(4-C6H4O(CH 2)5CH=CH2)2 (8; 32%). Reactions of PtCl2 with 1a,b, 2a-e,h,i, 4a,b (but not 4c,d), 5a,c-f,h, and 8 afford the corresponding bis(pyridine) complexes trans-10a,b (40-12%), trans-12a-e,h,i (84-46%), trans-17a,b (88-22%), trans-19a,c-f,h (94-63%), and trans-22 (96%). Selected adducts are treated with Grubbs′ catalyst and then H2 (Pd/C) to give trans-PtCl2[2,2′-(NC 5H4(CH2O(CH2)2n+2OCH 2)H4C5N)] (trans-11a,b; 79-63%), trans-PtCl2[3,3′-(NC5H4(CH 2O(CH2)2n+2OCH2)H4C 5N)] (trans-13,d,h,i; 93-80%), trans-PtCl2[2,6,2′, 6′-(NC5H3(CH2O(CH2) 2n+2OCH2)2H3C5N)] (trans-18a,b; 22-10%), trans-PtCl2[3,5,3′,5′-(NC 5H3(COO(CH2)2n+2OCO) 2H3C5N)] (trans-20d-f,h; 45-14%), and trans-PtCl2[3,5,3′,5′-(NC5H 3(4-C6H4O(CH2)12O-4- C6H4)2H3C5N)] (40%). A previously reported ring-closing metathesis of trans-PdCl2[2,6- NC5H3(CH2CH2CH=CH2) 2]2 is confirmed, and the new hydrogenation product trans-PdCl2[2,6,2′,6′-(NC5H 3((CH2)6)2H3C 5N)] (trans-16; 62%) is isolated. Additions of CH3MgBr to 12b,h and 13d,h afford the corresponding PtClCH3 species (94-41%), but analogous reactions fail with 2-substituted pyridine adducts. The reaction of trans-19c with PhC≡CH and CuI/i-Pr2NH gives the corresponding PtCl(C≡CPh) adduct (18%). The crystal structures of trans-17a, trans-11b, trans-13d, trans-13hCH2Cl2, trans-16, trans-18a,b, and trans-20e2CHCl3 are determined. Steric effects in the preceding data, especially involving 2-substituents and the MCl2 or MCl(X) rotators, are analyzed in detail.