A divergent construction of fused and bridged carbo-/heterocyclic scaffoldsviacascade reactions of aryl azomethine imines with vinyl cyclic carbonates

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1015 - 1021

Published: Jan. 1, 2023

Presented herein is a divergent synthesis of indene-fused pyrazoles and bridged benzodiazepines tethered with hydroxymethyl group through the cascade reactions aryl azomethine imines vinyl cyclic carbonates.

Language: Английский

---

Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2648 - 2652

Published: Jan. 1, 2023

Herein, we disclose the first Pd-catalyzed enantioselective (4 + 3) cycloaddition of N -2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate.

Language: Английский

---

Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4298 - 4302

Published: June 7, 2023

The synthesis of functionalized carbazoles as privileged nitrogen heterocycles has emerged a central topic in drug discovery and material science. We herein disclose the rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones 2-methylidene cyclic carbonate an allylating surrogate, resulting formation C2-formylated via tandem C–H allylation, [3 + 2] cycloaddition, aromatization, benzylic oxidation. synthetic utility this protocol is highlighted by variety post-transformations carbazoles.

Language: Английский

---

Rh(III)-Catalyzed C–H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3499 - 3508

Published: March 9, 2023

Rh(III)-catalyzed C-H/N-H annulation and C-H allylation of phenylindazolones have been realized by employing 5-methylene-1,3-dioxan-2-one 4-vinyl-1,3-dioxolan-2-one as scalable cross-coupling partners, delivering functionalized indazolone fused heterocycles branched linear allyl indazolones respectively in moderate to high yield. These divergent synthesis protocols showcase mild conditions, broad substrate scope, functional-group compatibility. In addition, scale-up preliminary mechanistic exploratory were also accomplished.

Language: Английский

---

Rh(iii)-Catalyzed tandem C(sp²)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(23), P. 6585 - 6590

Published: Jan. 1, 2021

A Rh( iii )-catalyzed tandem C(sp 2 )–H allylation/ N -alkylation annulation reaction of arene amides employing 5-methylene-1,3-dioxan-2-one as an efficient allyl source has been disclosed for the first time.

Language: Английский

---

Preparation of Mesoporous Chitosan Cobalt Supported Nano-Catalyst for the Catalyzed Reduction of Quinoline to N-formyltetrahydroquinoline

Catalysis Letters, Journal Year: 2025, Volume and Issue: 155(5)

Published: April 9, 2025

Language: Английский

---

Ruthenium(II)-Catalyzed Tandem C–H Allylation and [3 + 2] Dipolar Cycloaddition to Construct Bridged Tetracycles

Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8115 - 8119

Published: Oct. 31, 2022

The ruthenium(II)-catalyzed tandem C-H allylation and intramolecular dipolar cycloaddition between azomethine imines 2-methylidenetrimethylene carbonate is described herein. initially formed β-substituted allyl fragment could trigger the exotype [3 + 2] with polar group, resulting in formation of bridged tetracycles bearing a hydroxymethylene group at bridgehead carbon center. A wide substrate scope broad functional compatibility were observed. gram-scale synthesis synthetic transformations demonstrate utility this process.

Language: Английский

---

Rh(III)-Catalyzed [4 + 1] Annulation of Benzamides with Vinyl Cyclic Carbonates for the Synthesis of Isoindolinones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1304 - 1309

Published: Feb. 8, 2024

A Rh(III)-catalyzed C–H bond activation and subsequent [4+1] annulation of benzamides with vinyl cyclic carbonates have been developed for the synthesis isoindolinones, in which electron-rich alkenes could serve as one-carbon units. This reaction proceeds smoothly high regioselectivity under oxidant- silver-free conditions exhibits broad substrate scope functional group tolerance including some biological active materials. The scale-up derivatizations product further demonstrate potential synthetic utility this transformation.

Language: Английский

---

Modular Assembly of Pyrrolo[3,4-c]isoquinolines through Rh-Catalyzed Cascade C–H Activation/Annulation of O-Methyl Aryloximes with Maleimides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8447 - 8457

Published: June 4, 2024

An efficient and practical strategy for the construction of pyrrolo[3,4-

Language: Английский

---

Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5179 - 5184

Published: July 6, 2023

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports 1,2,3-benzotriazinones, triazinone ring remained intact in this C-H bond functionlization reaction. Also, denitrogenative could also be realized by changing reaction temperature. This protocol is featured high E selectivity, wide substrate scope, divergent structures products.

Language: Английский

---