Spiro Derivatives in the Discovery of New Pesticides: A Research Review

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(35), P. 10693 - 10707

Published: Aug. 23, 2022

Spiro compounds are biologically active organic with unique structures, found in a wide variety of natural products and drugs. They do not readily lead to drug resistance due their mechanisms action have, therefore, attracted considerable attention regarding pesticide development. Analyzing structure-activity relationships (SARs) summarizing the characteristics spiro high activity crucial steps design development new pesticides. This review mainly summarizes insecticidal, bactericidal, fungicidal, herbicidal, antiviral, plant growth regulating functions provide insight for creation compound

Language: Английский

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Atroposelective Construction of Nine‐Membered Carbonate‐Bridged Biaryls

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(31)

Published: May 27, 2022

Abstract We herein demonstrated an efficient method for the atroposelective construction of nine‐membered carbonate‐bridged biaryls through vinylidene ortho ‐quinone methide (VQM) intermediates. Diverse products with desirable pharmacological features were synthesized in satisfying yields and good to excellent enantioselectivities. In subsequent bioassays, several agents showed considerable antiproliferative activity via mitochondrial‐related apoptosis mechanism. Further transformations produced more structural diversity may inspire new ideas developing functional molecules.

Language: Английский

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Enantioselective Synthesis of Spirosilabicyclohexenes by Asymmetric Dual Ring Expansion of Spirosilabicyclobutane with Alkynes

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(48)

Published: Oct. 7, 2022

Silaspiranes have attracted particular attention due to their chiral spiro-silicon center, which serves as an ideal carbon isostere and can endow spiro-analogs with distinct properties. Distinct from previously reported cyclization or cycloaddition strategies form 5/5-silaspiranes, we report herein the asymmetric dual ring expansion of spirosilabicyclobutanes alkynes synthesize axially spirosilabicyclohexenes bearing a novel 6/6-silaspirane framework. DFT (density functional theory) calculations provide deep insight into origin high enantioselectivity controlled by sterically demanding binaphthyl phosphoramidite ligand. Preliminary studies chiroptical properties indicate that one spirosilabicyclohexene analogs exhibit fluorescence emission, Cotton effects CPL (circularly polarized luminescence) activity.

Language: Английский

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Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

RSC Advances, Journal Year: 2023, Volume and Issue: 13(47), P. 32858 - 32892

Published: Jan. 1, 2023

This review highlights recent developments in the microwave-assisted organic synthesis of N- and O-containing heterocycles with specific examples pyrazolopyrimidines-, coumarin-, quinoline-, isatin-based scaffolds their associated biological activities.

Language: Английский

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UV Light Is No Longer Required for the Photoactivation of 1,3,4-Oxadiazolines

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(3), P. 1964 - 1973

Published: Jan. 20, 2023

Carbenes play a key role in plethora of organic transformations. Although stabilized diazo carbonyl compounds predominate as source electrophilic carbenes, the hazardous nature nonstabilized analogues calls for their situ generation from stable precursors. Among these, 1,3,4-oxadiazolines serve diazoalkane surrogates under UV light irradiation. In view high stability, diverse reactivities, and straightforward synthesis, milder methodologies activation these that permit use UV-light-sensitive substrates are highly valued. Herein, we report visible-light-induced oxadiazolines by triplet energy transfer catalysis that, contrast to UV-induced processes, alters reactivity enables carbenes. The formed reactive species react with electron-poor olefins, thereby giving valuable spirocyclopropanes. Mechanistic investigations, both theoretical experimental, uncover plausible pathways highlight importance steps.

Language: Английский

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Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2784 - 2790

Published: April 23, 2024

Abstract Ytterbium triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri ‐annulated indole core. This process involves the formation imine and its (3+2)‐cross‐cycloaddition moiety, yielding tropane‐fused core under mild conditions. These products are significant interest for pharmacology as potential hybrid molecules dual mode action.

Language: Английский

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Simmons–Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates): Stereoselective Access to Functionalized Cyclopropyl Derivatives

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 7649 - 7657

Published: May 31, 2022

A Simmons-Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis(boronates) has been developed starting from corresponding alkenes. The resulting compounds were then subjected to regioselective Suzuki-Miyaura couplings produce diversely tri- or tetra-substituted arylcyclopropanes in good yields. Further functionalization with 2-lithiothiophene provided 1,2-bis(aryl)cyclopropanes.

Language: Английский

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Photogenerated donor–donor diazo compounds enable facile access to spirocyclopropanes

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(79), P. 11835 - 11838

Published: Jan. 1, 2023

Prompted by the increasing interest in strained hydrocarbons as potential drug candidates, we developed a simple and efficient photochemical protocol for (spiro)cyclopropanes from bench stable tosylhydrazones electron poor olefins. This two-step one-pot transformation proceeds (3+2)-cycloaddition of situ formed donor-donor diazo compounds, followed nitrogen extrusion Δ1-pyrazoline intermediates. Notably, kinetic analysis enabled isolation intermediary spiro-heterocycles.

Language: Английский

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The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(17), P. 3776 - 3790

Published: Jan. 1, 2021

This article covers ring expansions of vinylaziridines and vinyloxiranes developed over the past five years for accessing stereochemically enriched heterocycles.

Language: Английский

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Regioselective and stereospecific synthesis of functionalized 3,4-dihydro-2H-1,4-thiazines by catalyst-free [3 + 3] annulation of pyridinium 1,4-zwitterionic thiolates and aziridines

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4271 - 4276

Published: Jan. 1, 2022

An efficient route to 3,4-dihydro-2 H -1,4-thiazines was developed though [3 + 3] annulation of pyridinium 1,4-zwitterionic thiolates and aziridines under catalyst-free conditions.

Language: Английский

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