Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions

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

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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

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

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Diastereoselective Double Annulation of Allenoates with Povarov Adducts: Modular Synthesis of Multisubstituted Pyrroloquinolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16838 - 16849

Published: Nov. 6, 2024

Herein, we report an atom-economical, one-pot, four-component, diastereoselective double-annulation reaction to construct polyfused pyrroloquinolines. This highlights the cyclization of in situ

Language: Английский

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