Synthesis of 2,6-diaryl-1,2-dihydropyridines through a 6π-electrocyclization of N-sulfonylazatrienes

Resende, Diana I. S. P.; Guieu, Samuel; Oliva, Cristina Gómez de la; Silva, Artur M. S.

doi:10.1016/j.tetlet.2014.10.034

Cited by 13 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sequential DBU-promoted deprotonation of Int-II gives allene Int-III , which is followed by 6π-electrocyclization to form the intermediate Int-IV . It is assumed that AlCl 3 might act as a Lewis acid to promote this electrocyclization process . Finally, aromatization of Int-IV via abstraction of H from the proton pool and/or [1,7]- H migration afforded the product 3aa .…”

Section: Resultsmentioning

confidence: 99%

Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Guo

Zhao

et al. 2021

J. Org. Chem.

View full text Add to dashboard Cite

Polysubstituted 3-sulfonyl naphthalenes were constructed in good to high yields by AlCl 3 -mediated tandem reaction of 1,4-diyn-3-yl esters and sodium sulfinates. This reaction proceeded under mild reaction conditions and tolerated a variety of functional groups. Moreover, the mechanistic studies indicated that the initial formation of allene under DBU from 1,4-diyn-3-yl ester and a sequence of nucleophilic addition of sodium sulfinate, the formation of allene, and intramolecular cyclization might be involved.

show abstract

Section: Resultsmentioning

confidence: 99%

Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Guo

Zhao

et al. 2021

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Encouraged by this result, the use of 4‐toluenesulfonyl hydrazine was explored, with a frustrating outcome, since only 5 % of the expected isoquinoline was recovered, and no 3,4‐dihydroisoquinoline was observed (entry 2). Interestingly, the related N ‐sulfonylimines have been recently used in azatriene 6π‐electrocyclization reactions toward 1,2‐dihydropyridines…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polysubstituted 3‐Methylisoquinolines through the 6π‐Electron Cyclization/Elimination of 1‐Azatrienes derived from 1,1‐Dimethylhydrazine

2018

View full text Add to dashboard Cite

A convenient one pot microwave‐assisted 6π‐electron cyclization/aromatization approach toward 3‐methylisoquinolines is reported. The starting 1‐azatriene derivatives were prepared in situ by reaction of 2‐propenylbenzaldehydes with 1,1‐dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4‐dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.

show abstract

“…First, [1,5]-H migration of the Sonogashira coupling product 6 afforded the intermediate Int -1 , which was followed by 6π-electrocyclization to generate the intermediate Int -2 . It is assumed that Pd(OAc) 2 might act as a Lewis acid to promote this electrocyclization process . Finally, aromatization of the intermediate Int -2 via [1,7]-H migration afforded product 3 .…”

Section: Resultsmentioning

confidence: 99%

Construction of Substituted Benzenes via Pd-Catalyzed Cross-Coupling/Cyclization Reaction of Vinyl Halides and Terminal Alkynes

Xie

Wang

et al. 2016

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Synthesis of 2,6-diaryl-1,2-dihydropyridines through a 6π-electrocyclization of N-sulfonylazatrienes

Cited by 13 publications

References 42 publications

Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Synthesis of Polysubstituted 3‐Methylisoquinolines through the 6π‐Electron Cyclization/Elimination of 1‐Azatrienes derived from 1,1‐Dimethylhydrazine

Construction of Substituted Benzenes via Pd-Catalyzed Cross-Coupling/Cyclization Reaction of Vinyl Halides and Terminal Alkynes

Contact Info

Product

Resources

About