N-Unsubstituted 1,2-benzothiazine 1,1-dioxides: Pd-catalyzed one-pot sonochemical access and in silico / in vitro evaluation against MtbCM DOI

Narender Addu,

Hinuja Miriyala,

Ravikumar Kapavarapu

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1301, P. 137345 - 137345

Published: Dec. 20, 2023

Language: Английский

Synthesis of Amide Enol 2-Iodobenzoates by the Regio- and Stereoselective Gold-Catalyzed Acyloxyalkynylation of Ynamides with Hypervalent Iodine Reagents DOI
Yaowen Liu, Martin C. Dietl, Chunyu Han

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(39), P. 7101 - 7106

Published: Sept. 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.

Language: Английский

Citations

19
Diorganyl Diselenides and Iron(III) Chloride Drive the Regio- and Stereoselectivity in the Selenation of Ynamides DOI
Tales A. C. Goulart, Davi F. Back, Sidnei Moura e Silva

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 980 - 994

Published: Dec. 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.

Language: Английский

Citations

26
Harnessing NHC/Base-Catalyzed Regiodivergent Oxidative Cyclization for Versatile Aminolactone Synthesis DOI

In-Seok Choi,

P. T. KIM,

Wonbin Ha

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(24), P. 15939 - 15947

Published: Nov. 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.

Language: Английский

Citations

8
Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reactions of Ynamides with t-Butyl Carbamates/Carbonates DOI
Pan Han,

Zhuo‐Ya Mao,

Ming Li

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(7), P. 4740 - 4752

Published: March 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.

Language: Английский

Citations

22
Recent developments by zinc based reagents/catalysts promoted organic transformations DOI

Shaik Mohammed Ghouse,

Chinnabattigalla Sreenivasulu, Dakoju Ravi Kishore

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 105, P. 132580 - 132580

Published: Nov. 24, 2021

Language: Английский

Citations

14
Electrophile promoted cyclization of ortho-aryl substituted ynamides: construction of 3-amino-4-halo- or 4 seleno-isocoumarin derivatives DOI

Loïc Habert,

Iryna Diachenko, Pascal Retailleau

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(30), P. 6623 - 6627

Published: Jan. 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 via an electrophilic cyclization of ortho-ynamidyl benzoate esters.

Language: Английский

Citations

11
Palladium-Catalyzed Cascade 5-endo-dig Cyclization of Ynamides to Form 4-Alkynyloxazolones DOI
Tales A. C. Goulart, Davi F. Back, Sidnei Moura e Silva

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 3341 - 3351

Published: Feb. 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.

Language: Английский

Citations

8
A Short‐Cut to Substituted Fused Pyrrolo[2,1‐c][1,4]oxazines: A Hybrid Theoretical and Experimental Study DOI
А. В. Иванов, Alexander S. Bobkov, Svetlana V. Martynovskaya

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: May 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.

Language: Английский

Citations

4
Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors DOI
Mengyu Li, Song Li,

Liya Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9926 - 9930

Published: Nov. 12, 2024

We herein introduce glycosyl

Language: Английский

Citations

1
A facile synthesis of 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines from N-propargylic β-enaminones DOI
Özge İbiş, Metin Zora

Tetrahedron, Journal Year: 2020, Volume and Issue: 76(48), P. 131650 - 131650

Published: Oct. 16, 2020

Language: Английский

Citations

10