A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation–methoxylation reactions of selenium dihalides

Мусалов, М. В.; Yakimov, V. A.; Потапов, В. А.; Амосова, С. В.; Bоrodinа, Tatyana N.; Зинченко, С. В.

doi:10.1039/c9nj04707g

Cited by 21 publications

(30 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chalcogenated propargyl aryl ethers 79 underwent regioselective electrophilic intramolecular cyclizations by using I 2 , ICl, PhSeBr or BuTeBr 3 as electrophilic source, successfully afforded the substituted 3-halo-4chalcogen-2H-benzopyran 80 derivatives (Scheme 29). [65][66][67][68]…”

Section: Synthesis Of 3-halo-4-chalcogen-2h-benzopyranmentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

show abstract

Section: Synthesis Of 3-halo-4-chalcogen-2h-benzopyranmentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…In addition, Potapov et al have described an annulation reaction of selenium dichloride with propargyl and allyl phenyl ethers of formula 11 and 12, respectively, to produce oxaselenine heterocycles 14 and 15 via an electrophilic aromatic substitution, which would involve intermediates such as 13. [29][30][31] The latter reaction, which employs selenium chloride as a chalcogen source, is of limited scope.…”

Section: Scheme 1 Preparation Of Benzylsulfinyl Cyanide From Benzyl Tmentioning

confidence: 99%

“…Turne 28 and the synthesis of halogen-containing oxaselenine derivatives developed by Potapov et al [29][30][31] In fact, seleno-annulations can be considered as interesting reactions that are not well studied in spite of being useful for the preparation of selenium-containing heterocycles. At the present time, some five-membered rings bearing a selenium atom in their structure have been described, 21,30,32 in particular, very recently Ranu et al have developed an interesting one-pot method of preparation of benzo[b]selenophenes of general formula 16 starting from bromovinylbenzene derivatives of general formula 17.…”

Section: Scheme 3 First Selenine Preparation Carried Out By Thomson Andmentioning

confidence: 99%

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[b][1,4]-oxaselenines Formation from Selenocyanates

et al. 2020

View full text Add to dashboard Cite

An expedient preparation of selenium-containing heterocycles via an m-chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

show abstract

“…The laboratory of organochalcogen compounds of the A. E. Favorsky Irkutsk Institute of Chemistry develops effective approaches to novel chalcogen heterocycles by regioselective cyclization and annulation reactions of chalcogen-containing reagents [ 21 , 22 , 23 , 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides

2021

Self Cite

View full text Add to dashboard Cite

Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied. The opposite regiochemistry was observed in the reactions with vinyl chalcogenides and tetravinyl silane. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.

show abstract

A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation–methoxylation reactions of selenium dihalides

Abstract: A novel methodology for accelerating the annulation was developed based on the reactions of selenium dihalides in the presence of alcohols.

Cited by 21 publications

References 46 publications

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[b][1,4]-oxaselenines Formation from Selenocyanates

Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides

Contact Info

Product

Resources

About