74796-71-7

Upstream product

• 882029-80-3 p-toluenesulfonic acid 3,5-dibromo(pyridin-2-yl) ester 
• 98-80-6 phenylboronic acid 
• 13472-81-6 3,5-dibromo-2-hydroxypyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 150-30-1 Phenylalanine 
• 2835-06-5 phenylglycin 
• 4452-11-3 1,2-diphenylprop-2-en-1-one 
• 100-42-5 styrene 
• 622-79-7 benzyl azide 
• 886-65-7 1,4-diphenyl-1,3-butadiene 
• 2935-35-5 (S)-2-phenylglycine 
• 122-78-1 phenylacetaldehyde 
• 125877-36-3 1,4-diphenyl-2-aza-1,3-butadiene 
• 7182-10-7 N-(1-buten-1-yl)piperidine 

Relevant academic research and scientific papers

Synthesis of 2,5-bis-arylpyridines by [4 + 2] cycloaddition of 1,4-bis aryl-2-aza-1,3-butadienes with electron-poor dienophiles

Tetrahydropyridines 4a, 4b, 4c and pyridines 7a, 7b, 7c, 9a, 9b, 9c were synthesized by a [4 + 2] cycloaddition between 1,4-bis aryl-2-aza-1,3- butadienes and electron-poor dienophiles. Dimeric cycloadducts 6a, 6b, 6c, were also isolated indicating a competition between the expected Hetero Diels-Alder and a dimerization process.

N-Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted Pyridines

A modular and selective synthesis of mono-, di-, tri-, tetra-, and pentasubstituted pyridines is reported. Hydroamination of alkynes with N-silylamine using a bis(amidate)bis(amido)titanium(IV) precatalyst furnishes the regioselective formation of N-silylenamines. Addition of α,β-unsaturated carbonyls to the crude mixtures followed by oxidation affords 47 examples of pyridines in yields of up to 96%. This synthetic route allows for the synthesis of diverse pyridines containing variable substitution patterns, including pharmaceutically relevant 2,4,5-trisubstituted pyridines, using this one-pot protocol.

Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines

An oxidative trimerization of three amino acids has been realized to furnish 2,3,5-trisubstuitued pyridines in both cross- and homo-trimerization types. This method is capable of converting simple linear biomass material to heterocycles, which features in

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki–Miyaura Coupling of 3,5- and 4,6-Dibromo-2-tosyloxypyridines

Chemoselective Suzuki–Miyaura reactions on 3,5- and 4,6-dibromo-2-tosyloxypyridines have been studied for the preparation of trisubstituted pyridines. The optimized conditions allow for a facile access to 3,5- and 4,6-diaryl-2-tosyloxypyridines in yields of 8 to 99%. Further functionalization such as palladium-catalyzed amination and copper-free Sonogashira reaction of the tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biologically relevant trisubstituted pyridines. The formal synthesis of ficuseptine, a bioactive alkaloid, has also been achieved via the palladium-catalyzed cross-coupling reaction of 3,5-dibromo-2-tosyloxypyridine in 5 steps from 3,5-dibromo-2-hydroxypyridine with 50% overall yield. (Figure presented.).

Synthesis of Polysubstituted Imidazoles and Pyridines via Samarium(III) Triflate-Catalyzed [2+2+1] and [4+2] Annulations of Unactivated Aromatic Alkenes with Azides

Samarium(III) triflate-catalyzed [2+2+1] and [4+2] annulations have been identified for the preparation of fully substituted imidazoles and 2,3,5-trisubstituted pyridines from the readily available unactivated aromatic alkenes and azidomethyl aromatics. T

A metal-free decarboxylative cyclization from natural α-amino acids to construct pyridine derivatives

A metal-free decarboxylative cyclization from natural α-amino acids was developed and applied in the preparation of pyridine derivatives. By virtue of this method, a series of pyridines containing the moiety of natural α-amino acids can be synthesized efficiently from the corresponding natural α-amino acids. The Royal Society of Chemistry.

Novel Synthesis of 3,5-Disubstituted Pyridines by 1,4-Cycloaddition of 1-Aza-1,3-butadienes with Enamines

A new method for the synthesis of 3,5-disubstituted pyridines is described.Reactions of the N-substituted methanimines 1 with the β-substituted enamines 2 give 1-aza-1,3-butadienes 3a-3i and/or symmetrically 3,5-disubstituted pyridines 4a-c,e-h in moderate to good yields.At reaction temperatures of 150 deg C the azadienes 3 are the predominant products, and the reaction provides a good route to 1-azadienes with no substituent at the 4-position.At reaction temperatures of 200 deg C, and particularly using N-tert-butylmethanimine 1a and p-toluenesulfonic acid catalyst, the principal products are symmetrically 3,5-disubstituted pyridines.The cycloaddition was shown to proceed via the azabutadiene intermediate 3.Reactions of 3 with the enamines 2 lead to unsymmetrically 3,5-disubstituted pyridines.The mechanisms of these cycloadditions are discussed.