Copper-Catalyzed Intramolecular Chalcogenoamination of Enynyl Azides: Synthesis of 5-Selenyl/Sulfenyl Nicotinates

Reddy, Chada Raji; Ranjan, Ravi; Prajapti, Santosh Kumar

doi:10.1021/acs.orglett.8b03695

Cited by 37 publications

(35 citation statements)

References 65 publications

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“…Therefore, the synthesis of selenyl- and sulfenylpyridines has attracted considerable attention. In 2019, the Reddy group reported a copper-catalyzed aza-annulation of enynyl azides 1 for the synthesis of 5-selenyl- and sulfenylpyridine derivatives 18 and 19 ( Scheme 7 ) [ 51 ]. Diorganyl dichalcogenides (R 1 XXR 1 , X = Se, S) were used as selenyl and sulfenyl sources, respectively.…”

Section: Reviewmentioning

confidence: 99%

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Liu¹,

Luo²,

Fu³

et al. 2021

Beilstein J. Org. Chem.

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Great progress has been made in the tandem annulation of enynes in the past few years. This review only presents the corresponding reactions of 1,3-enyne structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly introduce the applications of the products and the reaction mechanisms for the synthesis of corresponding N-heterocycles.

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Section: Reviewmentioning

confidence: 99%

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Liu¹,

Luo²,

Fu³

et al. 2021

Beilstein J. Org. Chem.

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“…An efficient and catalytic system based on Cu(II) chloride and diorganyl diselenides or disulfides was employed to mediate the synthesis of 5-organochalcogenyl nicotinates 10 via intramolecular chalcogenoamination of enynyl azides (Scheme 10). 26 This methodology has tolerated the presence of aryl, aryl substituted and heteroaryl groups bonded to the terminal sp carbon of the enynyl azides and the use of diaryl and dialkyl dichalcogenides affording up to 98% yield of the heterocyclic compounds. The main advantages of this methodology include an atom-economic process since the use of less than 1 equivalent of the dichalcogenides has furnished the products in high yields, which indicates that both R 2 Y moieties are consumed during heterocycles formation.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Diorganyl Dichalcogenides and Copper/Iron Salts: Versatile Cyclization System To Achieve Carbo- and Heterocycles from Alkynes

et al. 2021

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Organochalcogen-containing cyclic molecules have shown several promising pharmacological properties. Consequently, different synthetic strategies have been developed to their obtaining in the last years. Particularly due to the low cost and environmental aspects, copper and iron-promoted cyclization reactions of alkynyl substrates have been broadly and efficiently applied to this purpose. In this way, this manuscript consists on an overview of the most recent advances in the synthesis of organochalcogen-containing carbo- and heterocycles by reacting diorganyl disulfides, diselenides and ditellurides with alkyne derivatives in the presence of copper and iron salts to promote cyclization reactions.

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“…The copper-catalyzed organochalcogenyl aza-annulation of enynyl azide 15 with diorganyl-dichalcogenides 4 successfully afforded the 5-selanyl/sulfenyl nicotinates 16 (Scheme 4). [22] The plausible mechanism shows that CuCl 2 will activate Ph 2 Y 2 4 (Y=Se or S) through polarization of the YÀ Y bond to Cu-complex, which encourages an electrophilic addition onto the alkyne that generate the intermediate 17.…”

Section: Synthesis Of 5-selanyl Nicotinate and 3-phenylselanyl Quinolinementioning

confidence: 99%

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

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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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.

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Copper-Catalyzed Intramolecular Chalcogenoamination of Enynyl Azides: Synthesis of 5-Selenyl/Sulfenyl Nicotinates

Cited by 37 publications

References 65 publications

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Diorganyl Dichalcogenides and Copper/Iron Salts: Versatile Cyclization System To Achieve Carbo- and Heterocycles from Alkynes

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

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