[1,5]-Oxy/Thio/Azole Sigmatropic Rearrangement versus Indolyl-Spirocyclization: Tandem Reactions of 2-Azidobenzoate with Isocyanides for Accessing Quinazolin-4(3H)-ones DOI
Shu Chen, Xin Wang,

Wenhui Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

A general protocol for the synthesis of a variety functionalized quinazolinones has been developed through sequential Pd-catalyzed coupling/1,5-alkyloxy/thio/azole shift/6π electrocyclization reaction isocyanides and 2-carbonylaryl azides. When 3-(2-isocyanoethyl)indoles were utilized, an unusual competitive between [1,5]-shift indole-spirocyclization was observed, which renders modular spiroindolenine-3,3'-pyrrolo[2,1-

Language: Английский

Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one DOI

Chun Xia Yang,

Bin Li, Peng Shi

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Language: Английский

Citations

3

Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions DOI
Han Wang, Xiaolong Ma, Lingyi Sun

et al.

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096

Published: Jan. 9, 2025

Language: Английский

Citations

2

Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

Citations

8

Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu, Xinying Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 694 - 694

Published: Jan. 1, 2025

Language: Английский

Citations

0

Development of indole hybrids for potential lung cancer treatment-part I: nitrogen-containing six-membered aromatic heterocycles DOI

Shijia Zhao,

Zhi Xu

Future Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 17

Published: March 29, 2025

Lung cancer is the most prevalent invasive malignancy and leading cause of cancer-related death. Chemotherapy vital for lung therapy, but multidrug resistance responsible majority fatalities, creating an imperative demand to develop novel chemotherapeutics. Indole a valuable anti-lung pharmacophore since its derivatives could act on cells through various mechanisms. Notably, indole hybrids inhibit multiple targets simultaneously have potential overcome shortcomings traditional Moreover, many such as indole-pyrimidine hybrid osimertinib indole-hydroxamic acid panobinostat, are either under clinical evaluations or already been approved therapy. This indicates that rational design represents highly prospective approach development new chemotherapeutic agents. review focuses exploring therapeutic delves into their action mechanisms well structure-activity correlations, covering articles published between 2021 present. The ultimate goal offer foundation in future.

Language: Английский

Citations

0

Thiolative Annulation of N-Benzyl-N-cyanopropiolamides Leading to Divergent Synthesis of Pyrroloquinazolin-1-ones and Maleimides DOI
Chada Raji Reddy,

Anootha Neeliveettil,

Uprety Ajaykumar

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

An unprecedented successive radical-promoted thiolative annulation/Pd-catalyzed C-H amination of N-benzyl-N-cyanopropiolamides to access pyrrolo[2,1-b]quinazolin-1(9H)-ones in a one-pot manner is described. Moreover, altering the step with oxidation (reagent switch) offered maleimides from same set readily accessible precursors. Both transformations display versatility across wide range substrates, enabling efficient various functionalized quinazolin-1-ones and good yields.

Language: Английский

Citations

0

Assembly of Selenadiazine Scaffolds via Rh(III)-Catalyzed Amidine-Directed Cascade C–H Selenylation/[5 + 1] Annulation with Elemental Selenium DOI

Yuyan Wan,

Chensi Li,

Zhensheng Lin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6625 - 6630

Published: Aug. 1, 2024

By employing elemental selenium as the source, we have realized amidine-directed Rh(III)-catalyzed cascade C–H selenylation/[5 + 1] annulation for direct construction of structurally novel selenadiazine, benzoselenadiazine, and benzoselenazol-3-amine frameworks with specific site selectivity good functional group tolerance. Besides, obtained products can serve fundamental platforms subsequent chemical transformations, thus, feasible SeNEx reaction, SeNEx/Michael addition, simple conversion selenadiazine product into diverse other organoselenium molecules were demonstrated accordingly. Taken together, developed methodology efficiently expands space species.

Language: Английский

Citations

2

Recent approaches for the synthesis of heterocycles from amidines via metal catalyzed C-H functionalization reaction DOI
Youpeng Zuo,

Pengfei Zuo,

Meijun Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5014 - 5031

Published: Jan. 1, 2024

Transition metal catalyzed C-H bond activation has become one of the most important tools for constructing new chemical bonds. Introducing directing groups to substrates is key a successful reaction, these can also be further transformed in reaction. Amidines with their unique structure and reactivity are ideal transition metal-catalyzed transformations. This review describes major advances mechanistic investigations activation/annulation tandem reactions amidines until early 2024, focusing on unsaturated compounds, such as alkynes, ketone, vinylene carbonate, cyclopropanols derivatives. Meanwhile this manuscript explores reaction different carbene precursors, example diazo azide, triazoles, pyriodotriazoles, sulfoxonium ylides well own activation/cyclization reactions. A bright outlook provided at end manuscript.

Language: Английский

Citations

0

α-Carbonyl Rh-Carbenoid Initiated Cascade Assembly of Diazobarbiturates with Alkylidene Pyrazolones for Synthesis of Spirofuropyrimidines DOI Creative Commons
Yue Zhang,

Yu‐Hang Mi,

Kuo Wang

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(13), P. 3178 - 3178

Published: July 3, 2024

Catalyzed by Rh2(esp)2 (10 mol%) and (±)-BINAP (20 in DCE at 80 °C, the cascade assembly between diazobarbiturates alkylidene pyrazolones proceeded readily produced spiro-furopyrimidines 38–96% chemical yields. The structure of prepared spirofuro-pyrimidines was firmly confirmed X-ray diffraction analysis.

Language: Английский

Citations

0

Ru(II)-Catalyzed Sustainable C–H Methylation of Indolines with Organoboranes in Ethanol DOI

Sumit Sharma,

Sachin,

Devesh Chandra

et al.

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

Published: Sept. 6, 2024

A sustainable protocol for Ru(II)-catalyzed regioselective C(sp

Language: Английский

Citations

0