Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

---

Cascade in Situ Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 4017 - 4023

Опубликована: Март 2, 2023

A facile cascade reaction for the site selective synthesis of 2-cyanochromones is described. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials I2/AlCl3 promoters, products are furnished via tandem chromone ring formation C–H cyanation. The in situ 3-iodochromone a formal 1,2-hydrogen atom transfer (HAT) process account unconventional selectivity. In addition, 2-cyanoquinolin-4-one has been realized by employing corresponding 2-aminophenyl enaminone substrate.

Язык: Английский

---

Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 109683 - 109683

Опубликована: Март 2, 2024

Язык: Английский

---

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Язык: Английский

---

Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3906 - 3912

Опубликована: Янв. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Язык: Английский

---

I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Год журнала: 2024, Номер 36(1), С. 109799 - 109799

Опубликована: Март 20, 2024

Язык: Английский

---

I₂-DMSO mediated dual α,β-C(sp²)–H functionalization/bicyclization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromone derivatives: chromeno[2,3-b]pyrrol-4(1H)-ones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4843 - 4847

Опубликована: Янв. 1, 2023

An unprecedented dual α,β-C(sp 2 )–H functionalization/bicyclization strategy of o -hydroxyphenyl enaminones for the preparation chromeno[2,3- b ]pyrrol-4(1 H )-ones has been established.

Язык: Английский

---

Tunable vicinal, geminal diphosphorylation and C–N bond phosphorylation of enaminones toward divergent phosphorylated ketone derivatives

Chemical Communications, Год журнала: 2023, Номер 59(42), С. 6383 - 6386

Опубликована: Янв. 1, 2023

The tunable reactions of enaminones with phosphine oxides/phosphonates in the form vicinal- and geminal diphosphorylation, C–N bond phosphorylation have been developed, providing new methods for synthesis divergent phosphorylated molecules.

Язык: Английский

---

Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3670 - 3675

Опубликована: Июль 2, 2024

Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as reaction partners o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists cascade iodination, chromone annulation, and Arbuzov‐type C−P cross coupling major transformations. In addition to providing enaminone‐based synthetic chromone‐3‐phosphonates, work shows advantage step economy skipping separate operation preparing iodo‐functionalized intermediate.

Язык: Английский

---

An Oxidative [3+2+1] Cyclization of Enaminones and N‐Alkenyl‐2‐pyrrolidinone: Access to Polysubstituted 4‐Alkylated 1,4‐dihydropyridines

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(8), С. 1217 - 1223

Опубликована: Март 25, 2023

Abstract An oxidative [3+2+1] cyclization of enaminones and N ‐alkenyl‐2‐pyrrolidinone is described for the synthesis 4‐alkylated 1,4‐dihydropyridines (1,4‐DHPs). By using terminal olefin as C4 source 1,4‐DHP skeleton, this synthetic strategy provides a series 1,4‐DHPs through 1,1‐difunctionalization/cyclization process. In protocol, two C( sp 3 )−C( 2 ) bonds )−N bond are simultaneously formed, hydrogen on newly formed methyl group skeleton confirmed possible mechanism proposed. magnified image

Язык: Английский

---