Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(15), P. 3101 - 3104

Published: Jan. 1, 2023

Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-naphthols in air is reported, which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation proceeds through ortho-quinone methide (o-QM) formation/Michael addition/dearomatization sequence, affording various spiro(naphthalenenaphtho)furan-2-ones moderate to excellent yields.

Language: Английский

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I₂-Promoted gem-Diarylethene Involved Aza-Diels–Alder Reaction and Wagner–Meerwein Rearrangement: Construction of 2,3,4-Trisubstituted Pyrimido[1,2-b]indazole Skeletons

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3386 - 3390

Published: May 8, 2023

A [3 + 1 2] cyclization–rearrangement reaction scheme was developed to synthesize pyrimido[1,2-b]indazoles from aryl methyl ketones, 3-aminoindazoles, and gem-diarylethenes. This metal-free process proceeds via a sequential aza-Diels–Alder Wagner–Meerwein rearrangement, possible mechanism demonstrated based on control experiments. method exhibits good substrate compatibility allows simple conditions. Moreover, the products display significant aggregation-induced emission characteristics after modifications.

Language: Английский

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I₂-DMSO-Mediated Construction of 2,3- and 2,4-Disubstituted Pyrimido[1,2-b]indazole Skeletons

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3941 - 3953

Published: Feb. 29, 2024

An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I2-DMSO-mediated substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation simple, the substrate scope wide. More than 60 derivatives have been synthesized, providing a new methodology related molecules potentially enriching bioactive-molecule libraries.

Language: Английский

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Construction of Pyrazolo[1,5-a]pyrimidines and Pyrimido[1,2-b]indazoles with Calcium Carbide as an Alkyne Source

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5822 - 5826

Published: Jan. 1, 2024

One-step construction of both 5-arylpyrazolo[1,5- a ]pyrimidines and 2-arylpyrimido[1,2- b ]indazoles using inexpensive, abundant easy-to-handle calcium carbide as solid alkyne source is depicted.

Language: Английский

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Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1430 - 1435

Published: Jan. 23, 2024

Abstract A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2 H ‐chromen‐2‐ones using N ‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights special roles which were not only used reactants but also an internal oxidant selectively activated ‐ α ‐C( sp 3 )−H bond. reaction features catalyst‐free, broad substrate scopes ( 27 examples 24 examples), operationally simple for one‐step synthesis, recovery recycling solvent.

Language: Английский

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Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(3), P. 780 - 785

Published: Dec. 9, 2022

Synthesis of multi-substituted pyridines and pyrroles was established involved C-N bond cleavage new C–N C–C formation. The adjacent to the primary carbon 1,2-diamino-2-methylpropane selectively cleaved.

Language: Английский

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Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Language: Английский

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Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-Dimethylaminoethanol as a One-Carbon Synthon for the Synthesis of 1,4-Dihydropyridines

Synthesis, Journal Year: 2024, Volume and Issue: 56(12), P. 1932 - 1940

Published: Jan. 9, 2024

Abstract A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where was applied as methine source. The procedure executed smoothly, resulting wide range with moderate to good yields. Additionally, these fluorophores exhibited photophysical characteristics.

Language: Английский

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Synthesis of Fused Pyrimidines from Azole Amines and Their Biological Activity

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(43)

Published: Aug. 3, 2024

Abstract Fused pyrimidines are a class of heterocyclic compounds that have gained considerable interest due to their extensive biological activities and potential applications in drug development. This review article aims provide comprehensive overview the latest synthetic approaches fused pyrimidines, including Michael reactions, multicomponent metal‐catalyzed photocatalytic peroxide‐mediated inverse electron demand Diels–Alder reactions. Furthermore, these compounds, such as ability combat cancer microbial infections, also discussed. summarizes existing literature on synthesis activity from 2020 2023. We hope this will inspire development more effective less toxic pyrimidine drugs with well‐designed structures.

Language: Английский

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Regioselective synthesis of 3,4-diarylpyrimido[1,2-b]indazole derivatives enabled by iron-catalyzed ring-opening of styrene oxides

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The first synthesis of 3,4-diarylpyrimido[1,2- b ]indazole derivatives enabled by the epoxide-opening reaction with 3-aminoindazoles has been realized.

Language: Английский

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