A novel strategy for the synthesis of 2-arylpyridines using one-pot 6π-azaelectrocyclization

Kobayashi, Tsunetoshi; Hatano, Sho; Tsuchikawa, Hiroshi; Katsumura, Shigeo

doi:10.1016/j.tetlet.2008.05.048

Cited by 32 publications

(7 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We herein report an efficient one‐pot procedure for the synthesis of substituted pyridines through a 6π‐azaelectrocyclization‐aromatization sequence in detail 17. The method is quite general for the substituents at the 2‐position of the pyridines, and a variety of aromatic‐ and olefin‐containing pyridines were rapidly constructed using the substituted vinyl stannanes, vinyl iodide, sulfonamides, and a palladium catalyst (see Scheme and Table 1).…”

Section: Introductionmentioning

confidence: 99%

Library‐directed Solution‐ and Solid‐phase Synthesis of 2,4‐Disubstituted Pyridines: One‐pot Approach through 6 π‐Azaelectrocyclization

Sakaguchi¹,

Kobayashi²,

Hatano³

et al. 2009

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

An efficient one-pot synthetic procedure for the synthesis of 2,4-disubstituted pyridines has been successfully established. The method proceeds through a 6pi-azaelectrocyclization-aromatization sequence. Using this method, a wide variety of pyridine structures substituted at the 2-position have been rapidly constructed from vinyl stannanes, vinyl iodide, sulfonamide, and a palladium catalyst. The method was further applied to the solid-phase synthesis wherein the use of a "traceless" sulfonamide linker enabled the rapid preparation of a small library of pyridines with high purity, without any chromatographic separation.

show abstract

Section: Introductionmentioning

confidence: 99%

Library‐directed Solution‐ and Solid‐phase Synthesis of 2,4‐Disubstituted Pyridines: One‐pot Approach through 6 π‐Azaelectrocyclization

Sakaguchi¹,

Kobayashi²,

Hatano³

et al. 2009

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

show abstract

“…In order to fine‐tune the opto‐electronic properties different synthetic protocols are available for example the well‐known formation of arylpyridines from aryl‐Grignard reagents and unsubstituted pyridine . Furthermore, 2‐phenylpyridines can be synthesized by cyclisation for example with diaminopropane and acetophenones catalyzed by copper or via a Pd‐catalyzed 6π‐azaelectrocyclization with vinylstananes, 4‐oxo‐crotonic acid ethyl esters and sulfonamides as nitrogen source . Another variant for building up phenylpyridines is an inverse electron demand retro Diels‐Alder reaction starting with 1.2.4‐triazenes .…”

Section: Methodsmentioning

confidence: 99%

Donor‐Acceptor Substituted 2‐Phenylpyridines by Means of Reductive C,C–Cross Coupling Reaction

et al. 2016

View full text Add to dashboard Cite

The preparation of 2‐phenylpyridines decorated with an electron donating and accepting unit, which are potentially suitable to induce second harmonic generation, was performed by means of reductive nickel catalyzed C,C‐cross coupling reaction, developed by Gosmini et. al. We were successful to obtain the desired 2‐phenylpyridines directly from donor‐functionalized arylhalides and acceptor‐modified 2‐halopyridines with a cheap and easy to prepare Ni catalyst. It turned out that even the presence of hydroxy groups and carboxylic acids are tolerated in this reaction, whereas in the case of a formyl group containing pyridine substrate no C,C‐coupled product was obtained. However, the coupling was successful when the formyl function was protected by an acetal formation.

show abstract

“…Intermediate B then undergoes a [1,3]‐H migration to yield oxime 4 ,. Esterification of oxime 4 with Ac 2 O generates compound 6 , which undergoes a 6πe‐azacyclization to yield intermediate C . Finaly, elimination of HOAc affords product 3 aa .…”

Section: Figurementioning

confidence: 99%

Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N‐Aryl Enamines

et al. 2018

View full text Add to dashboard Cite

An efficient and metal-free double CÀH bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key b-imino oxime ester intermediate. A quinoxaline derivative could be prepared from bcarbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps.

show abstract

A novel strategy for the synthesis of 2-arylpyridines using one-pot 6π-azaelectrocyclization

Cited by 32 publications

References 28 publications

Library‐directed Solution‐ and Solid‐phase Synthesis of 2,4‐Disubstituted Pyridines: One‐pot Approach through 6 π‐Azaelectrocyclization

Library‐directed Solution‐ and Solid‐phase Synthesis of 2,4‐Disubstituted Pyridines: One‐pot Approach through 6 π‐Azaelectrocyclization

Donor‐Acceptor Substituted 2‐Phenylpyridines by Means of Reductive C,C–Cross Coupling Reaction

Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N‐Aryl Enamines

Contact Info

Product

Resources

About