Journal of Molecular Structure, Год журнала: 2023, Номер 1301, С. 137345 - 137345
Опубликована: Дек. 20, 2023
Язык: Английский
Organic Letters, Год журнала: 2022, Номер 24(39), С. 7101 - 7106
Опубликована: Сен. 22, 2022
Multisubstituted alkenes are accessible by a gold-catalyzed acyloxyalkynylation of ynamides with ethynylbenziodoxolones (EBXs) perfect atom-economy. The EBX reagents transfer both the carboxylate as well alkynyl entity. Overall, this cascade comprises in situ generation an gold(III) species, stereoselective C(sp)-C(sp2) bond formation, and C-O coupling at position ynamides. This reaction proceeds under mild conditions accepts wide range substrates. A number tetrasubstituted amide enol 2-iodobenzoates bearing different functional groups were obtained good to excellent yields. DFT calculations explain observed regioselectivity. synthetic potential was further demonstrated selected follow-up transformations.
Язык: Английский
Процитировано
19
The Journal of Organic Chemistry, Год журнала: 2020, Номер 86(1), С. 980 - 994
Опубликована: Дек. 1, 2020
We report here our results on the application of ynamides as substrates in reactions with diorganyl dichalcogenides and iron(III) chloride to give selectively three different types compounds: E-α-chloro-β-(organoselenyl)enamides, 4-(organochalcogenyl)oxazolones, vinyl tosylates. The reveal that selectivity formation products was obtained by controlling functional groups directly bonded nitrogen atom ynamides. Thus, α-chloro-β-(organoselenyl) enamide derivatives were exclusively when TsN- MsN-ynamides treated a mixture diselenides (1.0 equiv) FeCl3 (3.0 dichloroethane (DCE, 3 mL), at room temperature. 4-(organochalcogenyl)oxazolones having an ester group, atom, upon treatment solution (1.5 dichloromethane (3 mL) Finally, tosylates from reaction p-toluenesulfonic acid. also studied prepared compounds for Suzuki Sonogashira cross-coupling reactions.
Язык: Английский
Процитировано
26
ACS Catalysis, Год журнала: 2023, Номер 13(24), С. 15939 - 15947
Опубликована: Ноя. 28, 2023
A regiodivergent oxidative cyclization of ynamide-tethered benzaldehydes has been achieved using an organocatalytic approach based on NHC/base. The method enables the efficient synthesis aminolactones with high regioselectivity, including formation 5-exo products through umpolung β-addition ynamides. reaction involves NHC-catalyzed aerobic oxidation benzaldehyde moiety followed by toward ynamide. Computational and experimental studies have shed light significance proton dissociation from in situ generated carboxylic acid determining regioselectivity reaction. synthetic versatility value obtained this are also highlighted.
Язык: Английский
Процитировано
8
The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(7), С. 4740 - 4752
Опубликована: Март 12, 2020
A highly regioselective approach to access amide enol carbamates and carbonates 5a–5c′, 7a–7h, 9 was developed through Cu(OTf)2-catalyzed reactions of ynamides 4 with t-butyl 2 8 6. Moreover, this strategy successfully applied generate 11a–11s 14a–14f from imides 10 13 an N-Boc cleavage–addition ring-opening process. range substituents amenable transformation, the desired were obtained in moderate good yields.
Язык: Английский
Процитировано
22
Tetrahedron, Год журнала: 2021, Номер 105, С. 132580 - 132580
Опубликована: Ноя. 24, 2021
Язык: Английский
Процитировано
14
Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(30), С. 6623 - 6627
Опубликована: Янв. 1, 2021
Isocoumarins
are
important
building
blocks
in
medicinal
chemistry.
An
access
to
3-amino-4-halo-
or
4-seleno-isocoumarins
a
short
time
(<1
min)
with
good
yields
was
reported
Язык: Английский
Процитировано
11
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3341 - 3351
Опубликована: Фев. 15, 2022
The selective synthesis of 4-alkynyloxazolones and their further applications as substrates to electrophile-promoted nucleophilic cyclization have been developed. reaction ynamides with terminal alkynes proceeded smoothly give in the presence a catalytic amount palladium(II) acetate. products were obtained sequential formation new C-C C-O bonds via cascade procedure. first step involved carbon-oxygen bond formation, 5-endo-dig closure, which was confirmed by X-ray analyses crystalline sample. Subsequently, an electrophilic selenium source gave 3-phenylselanyl benzofuran derivatives cyclization.
Язык: Английский
Процитировано
8
Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)
Опубликована: Май 22, 2023
Abstract The effect of substituents in the pyrrole ring and at triple bond on formation fused pyrrolooxazines from 1 H ‐pyrrol‐2‐ylmethanols propargyl chlorides has been theoretically experimentally studied. energy characteristics reaction are evaluated using quantum‐chemical calculations (CBS‐Q//B3). A one‐pot transition metal‐free synthesis substituted 3‐methyl‐1H‐pyrrolo[2,1‐ c ][1,4]oxazines good yields implemented superbasic system NaOH/DMSO.
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2024, Номер 26(46), С. 9926 - 9930
Опубликована: Ноя. 12, 2024
We herein introduce glycosyl
Язык: Английский
Процитировано
1
Tetrahedron, Год журнала: 2020, Номер 76(48), С. 131650 - 131650
Опубликована: Окт. 16, 2020
Язык: Английский
Процитировано
10