Diastereoselective Construction of Spirocyclic Isobenzofurans via a Tandem Michael Addition/5-Exo-dig Cyclization Reaction DOI

Shaghayegh Mehdidoust,

Saideh Rajai‐Daryasarei,

S. Sina Hosseini

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16613 - 16621

Published: Oct. 31, 2024

A practical approach for rapid and efficient access to spirocyclic isobenzofurans is described. The reaction proceeds through the cycloaddition of 1,6-ynenone derivatives 4-nitro-1,3-diarylbutan-1-ones, promoted by Cs

Language: Английский

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds DOI

Qianting Zhou,

Bin Li, Xinying Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(12), P. 2324 - 2338

Published: Jan. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Language: Английский

Citations

21
Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones DOI
Yuanshuang Xu,

Yujing Xiao,

Xinying Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 786 - 791

Published: Jan. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

Language: Английский

Citations

8
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 CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

Citations

6
Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles DOI

Manqing Wang,

Yuanshuang Xu,

Huihang Hou

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6536 - 6539

Published: Jan. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

Language: Английский

Citations

5
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
Ru(ii)-catalyzed regioselective [4 + 1] redox-neutral spirocyclization of aryl amidines with diazopyrazolones: direct access to spiro[indole-3,4′-pyrazol]-5′-ones DOI
Bo Cui,

Jian Shen,

Yadong Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1811 - 1816

Published: Jan. 1, 2024

An efficient protocol to construct spiro[indole-3,4′-pyrazol]-5′-ones via ruthenium( ii )-catalyzed selective C–H bond activation/[4 + 1] spirocyclization starting from easily available N -aryl amidines and diazopyrazolones has been developed.

Language: Английский

Citations

3
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

0
Condition‐Controlled Divergent Synthesis of Imidazoindolone Spiroisoquinolinones fromN‐Alkoxycarboxamide Indoles and Diazo Homophthalimides DOI

Manqing Wang,

Qianting Zhou,

Xinying Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1255 - 1261

Published: March 24, 2023

Abstract Presented herein is a condition‐controlled divergent synthesis of imidazoindolone spiro‐isoquinolinones (IISIQs) via the cascade reactions N ‐alkoxycarboxamide indoles with diazo homophthalimides. When reaction carried out under air and in absence an acid additive, IISIQ tethered ‐alkoxy moiety (IISIQ‐OR) formed through Rh(III)‐catalyzed C−H/N−H metalation, carbene formation/ migratory insertion followed by reductive elimination, which acts as oxidant to regenerate Rh(III) catalyst. run argon presence MesCO 2 H, on other hand, IISIQ−H rhodacycle intermediate formation, acid‐assisted intramolecular substitution/annulation N−O bond cleavge. In general, this method provides approach toward spiroheterocyclic scaffolds features accessible substrates, functional group compatibility external oxidant. Moreover, value developed protocol further showcased gram‐scale structural transformation products. magnified image

Language: Английский

Citations

7
One-Pot Synthesis of Indolin-3-ones Mediated by LiN(SiMe3)2/CsF DOI
Ruyuan Ma, Yuanyun Gu, Yan‐En Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5082 - 5086

Published: June 7, 2024

Indolin-3-ones are essential heterocycles with wide-ranging biological activities and medicinal values, therefore, efficient approaches to their synthesis remain in demand. Herein, a novel operationally simple method generate indolin-3-ones is reported by using tandem reaction of N-methylbenzylamines methyl 2-fluorobenzoates mediated the LiN(SiMe3)2 CsF system (34 examples, 30–85% yields). The C2-quaternary indolin-3-one further demonstrated potential practicability these reactions.

Language: Английский

Citations

2