Synthesis of 3-thiocyanated chromones via TCCA/NH4SCN-mediated cyclization/thiocyanation of alkynyl aryl ketones

Green Synthesis and Catalysis, Год журнала: 2021, Номер 3(2), С. 198 - 201

Опубликована: Дек. 24, 2021

3-Thiocyanated chromones was conveniently synthesized from alkynyl aryl ketones using commercially available, inexpensive trichloroisocyanuric acid (TCCA) as oxidant and NH4SCN thiocyanato (SCN) source. This metal-free approach is postulated to first in situ generate thiocyanogen chloride (Cl-SCN) the reaction of TCCA NH4SCN, followed by a rare efficient electrophilic thiocyano oxyfunctionalization alkynes enabled reactive species generated thereof.

Язык: Английский

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Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

Archiv der Pharmazie, Год журнала: 2021, Номер 355(3)

Опубликована: Ноя. 11, 2021

Abstract Acrylonitrile is a fascinating scaffold widely found in many natural products, drugs, and drug candidates with various biological activities. Several molecules such as entacapone, rilpivirine, teriflunomide, so forth, bearing an acrylonitrile moiety have been marketed. In this review, diverse synthetic strategies for constructing desired acrylonitriles are discussed, the different activities medicinal significance of derivatives critically evaluated. The information gathered expected to provide rational guidance development clinically useful agents from acrylonitriles.

Язык: Английский

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Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

Catalysts, Год журнала: 2022, Номер 12(1), С. 89 - 89

Опубликована: Янв. 13, 2022

Metal-catalyzed hydrofunctionalization reactions of alkynes, i.e., the addition Y–H units (Y = heteroatom or carbon) across carbon–carbon triple bond, have attracted enormous attention for decades since they allow straightforward and atom-economic access to a wide variety functionalized olefins and, in its intramolecular version, relevant heterocyclic carbocyclic compounds. Despite conjugated 1,3-diynes being considered key building blocks synthetic organic chemistry, this particular class alkynes has been much less employed when compared terminal internal monoynes. The presence two C≡C bonds adds classical regio- stereocontrol issues associated with alkyne processes’ other problems, such as possibility undergo 1,2-, 3,4-, 1,4-monoadditions well double reactions, thus increasing number potential products that can be formed. In review article, metal-catalyzed these challenging substrates are comprehensively discussed.

Язык: Английский

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Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Сен. 2, 2023

Abstract Sulfur‐containing alkynes, are important starting materials and intermediates in organic reactions. Some of sulfur‐containing alkynes display interesting bioactivities potentially applied as drugs. Various synthetic methodologies towards have been developed, including C(sp)−S coupling, thiolation, S ‐alkynylation, trifluoromethylthiolation, etc. In this review, the approaches alkynyl sulfides recent 3 years, well to form trifluoromethyl alkynylthiocyanates were highlighted. Firstly, property application introduced. After presenting superiority their methods classified presented details. According different kinds for sulfides, summarized proposed reaction mechanisms demonstrated if available.

Язык: Английский

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Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse (Z)-1,2-bis(arylthio)alkene derivatives

RSC Advances, Год журнала: 2021, Номер 11(46), С. 28447 - 28451

Опубликована: Янв. 1, 2021

An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes arylhydrazines with sodium thiosulfate (Na2S2O3) as the sulfur source for assembly functionalized (Z)-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl2 catalyst, a wide range are well tolerated, thus producing desired products in good yields functional group tolerance excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications organic synthesis material science.

Язык: Английский

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Chemoselective Preparation of Alkynes from Vicinal and Geminal Dibromoalkenes

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9817 - 9821

Опубликована: Ноя. 9, 2024

The reductive conversion of vicinal and geminal dibromoalkenes into the corresponding alkynes with

Язык: Английский

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Recent Advances in the Synthesis of Organic Thiocyano (SCN) and Selenocyano (SeCN) Compounds, Their Chemical Transformations and Bioactivity

Molecules, Год журнала: 2024, Номер 29(22), С. 5365 - 5365

Опубликована: Ноя. 14, 2024

New approaches for the synthesis of organic thio- and selenocyanates, methods to incorporate them into more complex structures, including a wide variety heterocyclic polycylic derivatives, are reviewed. Protocols that convert SCN SeCN moieties thio seleno derivatives by transforming cyano group also examined. In representative cases, bioactivity data these classes compounds

Язык: Английский

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Zinc‐Catalyzed Hydrocyanation of Ynamides and Photoisomerization, a General and Selective Access to E and Z Trisubstituted α‐Enamidonitriles

Chemistry - A European Journal, Год журнала: 2023, Номер 29(30)

Опубликована: Фев. 27, 2023

The fully regio- and stereoselective Zn-catalyzed hydrocyanation of ynamides is reported represents a general access to various trisubstituted E-α-enamidonitriles. catalyst-free photoisomerization selectively yields the energetically comparable Z-stereoisomer. Finally, synthetic potential these new α-enamidonitriles was evaluated through synthesis original heterocycles.

Язык: Английский

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Construction of a Functionalized Selenophene‐Allylidene Ligand via Alkyne Double Action at a Diiron Complex

European Journal of Inorganic Chemistry, Год журнала: 2020, Номер 2020(34), С. 3268 - 3276

Опубликована: Авг. 26, 2020

The diiron µ‐vinyliminium compounds [Fe 2 Cp (CO)(µ‐CO){µ‐η 1 :η 3 ‐C HC NMe(R)}]CF SO (R = Me, 2a ; R Xyl 2,6‐C 6 H Me , 2b η 5 ) reacted with grey selenium, in the presence of sodium methoxide, to give corresponding Se‐functionalized derivatives (Se)C NMe(R)}], 3a – b ca. 50 % yields. monoiron zwitterionic complex [FeCp(CO){SeC (NMe )C H}], 4 was obtained as a side‐product (31 %) reaction leading . treatment 3b S 8 /NaOMe afforded 2‐ferra‐thiophene [FeCp(CO){SC NMe(Xyl)}], 49 yield. straightforward reactions two‐fold excess dialkylacetylenedicarboxylates led functionalized 3‐amino‐selenophenes appended frame through bridging allylidene ligand, 7 (CO R)C SeC )}] 6a Et, 6b t Bu, 6c ), approximately synthesis c is result two distinct modes reactivity exhibited by alkyne reactant one pot, i.e. 1,3‐dipolar cycloaddition C and Se atoms insertion into Fe‐µ‐alkylidene. All products were characterized means elemental analysis, IR multinuclear NMR spectroscopy, molecular structure elucidated single‐crystal X‐ray diffraction study.

Язык: Английский

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Electrophilic Oxythio/selenocyanation of o‐Alkenyl Benzoic Acids: Divergent Synthesis of Thio/selenocyanated Isobenzofuranones and Isocoumarins

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(12)

Опубликована: Ноя. 17, 2022

Abstract A transition‐metal free thio/selenocyanation of o ‐alkenyl benzoic acids via the electrophilic Cl−S(Se)CN species, in‐situ generated from inorganic thio/selenocyanating salt and PhICl 2 , has been realized under mild reaction conditions. This protocol offers a divergent synthesis thio/selenocyanated isobenzofuranones isocoumarins, depending on substitution type substrates.

Язык: Английский

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