The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16564 - 16570
Опубликована: Окт. 31, 2024
An efficient method for phosphine-catalyzed sulfophosphinoylation of α,β-unsaturated ketones synthesis allylic organophosphorus compounds has been reported, in which acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond C-O obtain high regio- stereoselectivity moderate excellent yields.
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11562 - 11580
Опубликована: Июль 27, 2023
Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.
Язык: Английский
Процитировано
23
Sustainable Chemistry for the Environment, Год журнала: 2024, Номер 5, С. 100066 - 100066
Опубликована: Янв. 6, 2024
The one-pot, three-component cyclization reaction a wide variety of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-keto ester compounds was performed in simple manner. reactions carried out the presence sodium chloride (NaCl) as profitable, green, efficient catalyst at room temperature. Optimization experiments indicate that amount 17 mol% loaded NaCl is sufficient to catalyze reaction. Among advantages this NaCl-catalyzed method are availability catalyst, no need for synthesis several steps, commercially available reactants, use aqueous conditions, clean synthesis, non-inflammable medium, environmental pollution, safety, cost-effectiveness, pot-economy, optimum efficiency, carbon economy steps. Due absence harmful solvents, an abundant, low-cost, useful water solvent, considered green synthesis.
Язык: Английский
Процитировано
7
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4412 - 4439
Опубликована: Ноя. 16, 2023
Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.
Язык: Английский
Процитировано
14
Research on Chemical Intermediates, Год журнала: 2023, Номер 49(10), С. 4603 - 4619
Опубликована: Июль 9, 2023
Язык: Английский
Процитировано
10
Scientific Reports, Год журнала: 2025, Номер 15(1)
Опубликована: Апрель 30, 2025
The present investigation has introduced a new class of isocyanide/acetylene-based multicomponent reactions (IAMCRs). These are robust technique for efficiently synthesizing intricate spiro architectures through zwitterionic adduct. coupling reaction between the "in situ" generated dipoles isocyanide-acetylenic ester adducts and 3-alkyl-4-arylidene-isoxazol-5(4H)-one derivative presents highly effective synthetic pathway obtaining novel 1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene heterocycles. broad range substrates, standard experimental conditions, straightforward procedure, impressive yields make our catalyst-free three-component approach practical green, as it remarkably offers step-, time- cost-effectiveness based on green metrics.
Язык: Английский
Процитировано
0
ACS Catalysis, Год журнала: 2025, Номер unknown, С. 8303 - 8316
Опубликована: Май 2, 2025
Язык: Английский
Процитировано
0
New Journal of Chemistry, Год журнала: 2023, Номер 47(35), С. 16636 - 16642
Опубликована: Янв. 1, 2023
A general mechanistic map of the PPh 3 -catalyzed transformation reaction MBH carbonate has been theoretically studied and NCI ELF analyses are performed to disclose origins selectivities role catalyst, respectively.
Язык: Английский
Процитировано
9
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)
Опубликована: Май 27, 2024
Abstract A straightforward [3+2] annulation method for synthesizing bisspiro(oxindole) derivatives has been developed by using isatin‐derived Morita‐Baylis‐Hillman carbonates and p ‐quinone methides ( ‐QMs) with 4‐dimethylaminopyridine (DMAP) as the catalyst. The optimized protocol in dichloromethane (DCM) solvent achieves good yields (up to 87 %) diastereoselectivity (>20 : 1). versatility of is shown through synthesis various derivatives, including chiral variants up 82 % ee. intermediates were captured HRMS, a plausible reaction pathway was proposed.
Язык: Английский
Процитировано
2
ChemistrySelect, Год журнала: 2023, Номер 8(39)
Опубликована: Окт. 19, 2023
Abstract DABCO promoted one‐pot three‐component reaction of aromatic amines, dialkyl but‐2‐ynedioates and MBH nitriles isatins selectively afforded two diastereomeric spiro[indoline‐3,4′‐pyridines] in comparable yields. On the other hand, cyclization carbonates DCM at room temperature gave spiro[cyclopentane‐1,3′‐indoline] derivatives, while chloroform 70 °C resulted unique cyclopenta[ c ]quinolone derivatives with ring‐opening isatin moiety. A plausible mechanism was rationally proposed to explain formation different products.
Язык: Английский
Процитировано
4
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(25)
Опубликована: Апрель 8, 2024
Abstract A catalytic asymmetric (3+2) cyclization of pyrazolone‐based MBH adducts with alkylidenyl isoxazolones was presented by using DMAP‐derived chiral catalyst, affording bis‐spirocyclic pyrazolones bearing vicinal all‐carbon quaternary stereocenters within an imbedded cyclopentene ring scaffold in good yields excellent stereoselectivities under mild conditions.
Язык: Английский
Процитировано
1