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
Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 362(3), P. 438 - 461
Published: July 26, 2019
Abstract Recent continuing studies on the reactive small molecules of methylenecyclopropanes (MCPs) type and their derivatives have led to rapid development a variety efficient synthetic methods based novel reactions. These new transformations proved be very powerful tools access otherwise difficult‐to‐obtain molecules. Although there been some nice reviews applications MCPs, is still none focusing MCPs‐based construction carbocycles, which are class important skeletons in organic chemistry, pharmaceutical natural product synthesis, biochemistry, agrichemicals. Thus, this review an attempt summarize reports published since 2002 carbocyclic compounds starting from versatile hoping that it may fill gaps field. magnified image
Language: Английский
Citations
49
Organic Letters, Journal Year: 2020, Volume and Issue: 22(11), P. 4078 - 4082
Published: May 13, 2020
The generation of 2,3-dihydro-benzo[c][1,2]diazepine derivatives via rhodium(III)-catalyzed [4+3] annulation pyrazolidinones and propargylic acetates is disclosed. reaction proceeds smoothly under relatively mild conditions from as novel C3 synthons. A range dinitrogen-fused heterocyclic compounds are readily accessed by this approach.
Language: Английский
Citations
46
Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(22), P. 4861 - 4875
Published: Sept. 21, 2020
Abstract Benzazepines and benzodiazepines, benzofused seven‐membered N‐heterocycles, compose an important family of natural products pharmaceuticals. Although certainly effectives, classical synthetic methods these cyclic compounds involve methodologies that often require multistep procedures, with generation waste materials lack sustainability. By contrast, cycloadditions based on transition metal catalyzed C−H bond activations (oxidative annulations) have emerged as appealing strategies for more sustainable processes. In this review, we focus our attention to describe the state‐of‐the‐art transition‐metal‐catalyzed annulations via benzazepines benzodiazepines. magnified image
Language: Английский
Citations
46
Chemistry - An Asian Journal, Journal Year: 2019, Volume and Issue: 14(24), P. 4520 - 4533
Published: Sept. 18, 2019
Abstract Strained ring systems are regarded as privileged coupling partners in directed C−H bond functionalization and have emerged a potential research area organic synthesis. The inherent strain these acts driving force, allowing the facile construction of diversified structural scaffolds via integrating activation ring‐scission. mechanistic underpinnings allows implementation plethora bonds across plentiful substrates, including less reactive alkyl ones. Considering synthetic space, this will foster developments novel methods chelation guided functionalization. This review focus on recent transition‐metal catalyzed assisted concomitant scission strained rings to attain molecular complexity.
Language: Английский
Citations
43
Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(39), P. 21327 - 21333
Published: June 28, 2021
A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic trizazspiroheterocyclic scaffolds could be independently constructed by selective N-N cascade, C(sp2 )-H activation/[4+1] novel tandem )-H/C(sp3 strategy, along with broad scope substrates, moderate excellent yields valuable transformations. More importantly, in these transformations, we are the first time capture activation C(sp3 pyrazolidinones under different system.
Language: Английский
Citations
35
Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(12), P. 4543 - 4549
Published: March 17, 2021
We report here a C–H homoallylation reaction of aromatic ketones with methylenecyclopropanes (MCPs) only using catalytic amount Fe(PMe3)4. A variety and MCPs are applicable to the form ortho-homoallylated selectively via regioselective scission three-membered rings. The homoallylated products amenable further elaborations, providing functionalized 1,2-dihydronaphthalenes.
Language: Английский
Citations
34
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(24)
Published: March 26, 2022
Abstract Despite the widespread existence of chiral 1,4‐diamines in bioactive molecules and their applications asymmetric catalysis, catalytic synthesis such structures from readily accessible substrates remains a long‐standing challenge. Here, we report Cu‐catalyzed cascade hydroamination protocol to construct wide range 1,4‐diamine derivatives high yields with excellent enatioselectivities (up 95 % yield up >99 ee). The use two hydroxylamine esters containing different functionalized amino groups allowed us increase complexity final structures. desired products could be easily transformed into NH 2 ‐Terfenadine. Mechanistic study demonstrates that this reaction proceeds through ring‐opening sequence.
Language: Английский
Citations
26
Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2582 - 2587
Published: April 10, 2023
Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides via C-centered [1,2]-rearrangement have been developed. The imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition in situ generated bicyclic diaziridine, which facilitated the subsequent annulations presence different metal complexes catalysts. benzo[c]chromen-1-one pyrano[de]isochromene scaffolds could be independently constructed Rh(III) Ru(II), respectively. It was worth noting that employed first DG through rearrangement progress.
Language: Английский
Citations
14
Organic Letters, Journal Year: 2019, Volume and Issue: 21(6), P. 1789 - 1793
Published: Feb. 22, 2019
Chemodivergent annulative couplings have been realized between N-methoxy benzamides and 1,3-enynes via Rh-catalyzed C-H activation 1,4-Rh migration. Under Rh/copper catalyzed aerobic conditions, the nitrogen annulation occurred as major pathway. The chemoselectivity was switched to oxygen under proper condition control with stoichiometric amounts of Cu(II) oxidant NaOAc. Both coupling systems proceeded a broad scope functional group tolerance.
Language: Английский
Citations
37
Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(12), P. 2897 - 2903
Published: March 27, 2019
Abstract Herein, we report a Rh(III)‐catalyzed 1,3‐dienylation of isoquinolin‐1(2 H )‐ones through C−H activation. The present reaction enables the preparation 3‐(buta‐1,3‐dien‐2‐yl)isoquinolin‐1(2 direct cross‐coupling readily available with methylenecyclopropanes, while tolerating many sensitive functional groups. Therefore, this method provides an efficient and convenient approach for modification interesting molecules. magnified image
Language: Английский
Citations
37