Water-Controlled Geminal Hydroxyphosphinoylation and Diphosphinoylation of Enaminones with H-Phosphine Oxides DOI

Qiang Huang,

Xin Jin, Huabin Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

A water-controlled geminal phosphinoylation of enaminones with H-phosphine oxides has been established through AlCl3-mediated C-N bond cleavage in this work, which provides a novel strategy for accessing various hydroxy and diphosphinoyl products 3a 4a high yields. The transformation features excellent functional group tolerance, operational simplicity, atom economy, is amenable complex molecule skeletons. Preliminary mechanism studies suggest the conversion from to involve elimination hydroxyl group, water temperature plays critical role influencing reaction pathway product selectivity. This research significant value functionalization enaminones.

Язык: Английский

Base-Controlled Synthesis of Heteroatom-Embedded 9-Membered Cycloalkynes and 6-Membered Sultams through Copper-Catalyzed Cyclization DOI
Haoyang Liu,

H Xing,

Ping Yu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(2), С. 984 - 993

Опубликована: Янв. 7, 2025

A facile copper-catalyzed, base-controlled cyclization reaction has been developed for the synthesis of 9-membered cycloalkyne and 6-membered heterocycle sultams under mild conditions. This protocol utilizes a copper-catalyzed intramolecular A3 (alkyne–aldehyde–amine) coupling to efficiently synthesize in yields up 90%. Alternatively, by substituting NaHCO3 with DBU, achieves selective deprotection N-propargyl group, thereby facilitating formation heterocyclic sultams, also high yields.

Язык: Английский

Процитировано

0

Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines DOI Creative Commons
Ting Chen, Ting Huang,

Mao-Chun Ye

и другие.

Molecules, Год журнала: 2025, Номер 30(2), С. 350 - 350

Опубликована: Янв. 16, 2025

In this study, we present the HOAc-catalyzed selective cleavage of C=C double bond enaminones, enabling formation a new C–N and C=N for one-pot synthesis 2-substituted 3,4-dihydroquinazolines directly from ynones 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free oxidant-free conditions, offering sustainable efficient approach with broad functional group tolerance.

Язык: Английский

Процитировано

0

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

и другие.

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Organic Base-Catalyzed Cascade Reaction of CF3–Iminopropargylic Alcohols with Carboxylic Acids: an Approach to β-CF3 β-Aminoenones DOI
Ruslan S. Shulgin,

O. G. Volostnykh,

А. В. Степанов

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 6, 2025

A novel approach to the synthesis of β-CF3 β-aminoenones by organic amine base-catalyzed reaction CF3-iminopropargylic alcohols with carboxylic acids is reported. The advantages protocol are ease operation, available starting materials, and simple tertiary catalysts.

Язык: Английский

Процитировано

0

Water-Controlled Geminal Hydroxyphosphinoylation and Diphosphinoylation of Enaminones with H-Phosphine Oxides DOI

Qiang Huang,

Xin Jin, Huabin Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

A water-controlled geminal phosphinoylation of enaminones with H-phosphine oxides has been established through AlCl3-mediated C-N bond cleavage in this work, which provides a novel strategy for accessing various hydroxy and diphosphinoyl products 3a 4a high yields. The transformation features excellent functional group tolerance, operational simplicity, atom economy, is amenable complex molecule skeletons. Preliminary mechanism studies suggest the conversion from to involve elimination hydroxyl group, water temperature plays critical role influencing reaction pathway product selectivity. This research significant value functionalization enaminones.

Язык: Английский

Процитировано

0