Rh(III)‐Catalyzed C−H Annulation of 3‐Aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxides with Vinylene Carbonates DOI Open Access

Chaitanya Ittamalla,

D. Yogananda Chary,

Balasubramanian Sridhar

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(4)

Published: Nov. 22, 2023

Abstract A novel method has been developed for the synthesis of fused dihydroisoquinoline frameworks through a Rh(III)‐catalyzed annulation 3‐aryl‐2 H ‐benzo[ e ][1,2,4]thiadiazine‐1,1‐dioxides with vinylene carbonates by C−H bond activation. This is first report on oxidative functionalization aryl‐2 ][1,2,4]thiadiazine‐1,1‐dioxide carbonate to afford angularly heterocycles in good yields high functional group tolerance. In this approach, acts as glycolaldehyde surrogate construct ring systems.

Language: Английский

Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate DOI
Jiang Nan, Qiong Huang,

Xinran Men

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(26), P. 3571 - 3574

Published: Jan. 1, 2024

Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments

Language: Английский

Citations

4

Recent Advances in the Synthesis of Nitrogen‐Containing Heterocycles Based on Hydrazine‐Directed C−H Bond Activation/Annulation Reactions DOI Open Access
He Li, Tao Chen, Bin Wu

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

Abstract Nitrogen‐containing heterocyclic compounds are the core skeletons of many natural products, bioactive molecules and drugs, transition metal‐catalyzed hydrazine‐directed C−H bond activation/annulation reactions is one effective methods for synthesis nitrogen‐containing compounds. In this review, important research progress activation reviewed according to size constructed heterocycles, substrate scope reaction mechanism discussed in detail, limitations future development prospects summarized outlooked.

Language: Английский

Citations

0

Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent DOI
Jiang Nan, Hanqing Zhang, Lanxin Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Language: Английский

Citations

0

Carboxylic Acid-Enabled Vinylene Transfer Reaction by Co(III) Catalyst: Scope and Applications to the Five-Step Total Synthesis of Protoberberine Alkaloids Containing Free Hydroxyl Group without Protection DOI
Ying Song, Ruimin Li,

Jintong Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3238 - 3250

Published: Feb. 14, 2024

A Co(III)-catalyzed vinylene transfer reaction enabled by carboxylic acid is presented. This redox-neutral transformation tolerates various functional groups, including free hydroxyl and features practicality. Five-step routes based on the Heck annulation have been devised to total synthesis of 8-oxodehydrodiscretamine 2-demethyl-oxypalmatine without protection functionality.

Language: Английский

Citations

3

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives DOI Creative Commons
Yi‐Chun Chen,

Ziqi Lu,

Wenfen He

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(7), P. 4804 - 4809

Published: Jan. 1, 2024

The step-economical synthesis of C2, C3-unsubstituted 1-aminoindole derivatives through rhodium-catalyzed annulation hydrazines with vinylene carbonate.

Language: Английский

Citations

2

Rh(III)- or Ru(II)-Catalyzed C–H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones DOI
Yuqin Wang,

Yiling Zeng,

Yi Xiao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 19, 2024

Transition metal-catalyzed C-H annulation reactions have been extensively utilized for the synthesis of cinnolines, especially N-protected ones; however, none them can yield cinnolin-4(1

Language: Английский

Citations

2

Simultaneous intramolecular and intermolecular coupling of polar bond vibrations induced spectral splitting phenomenon DOI
Qian Peng, Zian Wang, Bin‐Bin Xie

et al.

Journal of Molecular Liquids, Journal Year: 2024, Volume and Issue: 401, P. 124719 - 124719

Published: April 12, 2024

Language: Английский

Citations

1

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates DOI

Yihui Mao,

X.‐S. Wang,

Chengcheng Zhong

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(16), P. 4464 - 4469

Published: Jan. 1, 2024

A visible-light-induced oxytrifluoromethylation reaction of carbamate-containing alkenes has been reported for the synthesis diverse cyclic carbonates and vicinal diols bearing trifluoroethyl substituted quaternary centers.

Language: Английский

Citations

1

Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate DOI
Jianbo Ma, Yiyong Yin,

Xing-Mei Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

We developed a cascade C–H activation/[3 + 2] annulation for enaminones and vinylene carbonate, employing the catalyst [Cp*RhCl 2 ] oxidants. This reaction allows efficient synthesis of 3-carbonylpyrroles.

Language: Английский

Citations

1

Programmable Synthesis of Cationic Azaperylenes via Rh(III)-Catalyzed Multiple C–H/N–H Bonds Activation and Annulation DOI
Hui Li,

Yiling Zeng,

Fangpeng Liang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11179 - 11183

Published: Dec. 17, 2024

Rh(III)-catalyzed dual N-H and triple C-H activation/(4 + 2) annulation of 2-aryl-2,3-dihydro-1

Language: Английский

Citations

1