Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(9)

Published: Feb. 8, 2024

Abstract Cycloalkanols ring‐opening transformation is one of the most valuable and wide area research. Among numerous methods that have been developed, transition‐metal‐free approaches attracted great interest from both chemists pharmacologists. This largely due to advantages being environmentally benign, cost‐effective operationally simple. Here we provide a comprehensive outline on recent advances in synthesis distally substituted ketones cyclic compounds via cycloalkanols under conditions.

Language: Английский

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Visible-light-induced denitrogenative phosphorylation of benzotriazinones: a metal- and additive-free method for accessing ortho-phosphorylated benzamide derivatives

Green Chemistry, Journal Year: 2020, Volume and Issue: 23(1), P. 296 - 301

Published: Dec. 10, 2020

The first metal-free, visible-light-induced denitrogenative phosphorylation of 1,2,3-benzotriazinones is presented.

Language: Английский

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Construction of Bicyclic 1,2,3-Triazine N-Oxides from Aminocyanides

Organic Letters, Journal Year: 2020, Volume and Issue: 23(3), P. 734 - 738

Published: Dec. 15, 2020

Using a facile and cost-effective method, nine bicyclic 1,2,3-triazine 2-oxides were synthesized from o-aminocyanide substrates through an unusual nitration cyclization. The reaction mechanism was studied experimentally theoretically. Moreover, 3-oxides also obtained in good yields.

Language: Английский

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Ag-Catalyzed ring-opening of tertiary cycloalkanols for C–H functionalization of cyclic aldimines

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(12), P. 1506 - 1509

Published: Jan. 1, 2021

Silver-catalyzed direct C–H functionalization of cyclic aldimines with cyclopropanols and cyclobutanols via a radical-mediated C–C bond cleavage strategy has been realized, generating the desired products in decent yields wide substrate scope.

Language: Английский

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Rh-Catalyzed cascade C–H activation/C–C cleavage/cyclization of carboxylic acids with cyclopropanols

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(48), P. 5929 - 5932

Published: Jan. 1, 2021

Merging both C–H and C–C activation in a tandem process is highly appealing but marked challenge.

Language: Английский

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Nickel-Catalyzed, Manganese-Assisted Denitrogenative Cross-Electrophile-Coupling of Benzotriazinones with Alkyl Halides for ortho-Alkylated Benzamides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(31), P. 5741 - 5745

Published: Aug. 2, 2022

A nickel-catalyzed denitrogenative cross-electrophile-coupling of benzotriazinones with unactivated alkyl halides (X = Cl, Br, I) in the presence manganese powder as a reductant has been developed. The reaction furnishes ortho-alkylated secondary benzamides modest to good yields under mild conditions. scope is demonstrated 25 examples, showing tolerance steric hindrance and common functional groups, thus providing an efficient protocol benzamide derivatives without use preprepared organometallic reagents.

Language: Английский

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Trifluoroacetic Acid-Mediated Denitrogenative ortho-Hydroxylation of 1,2,3-Benzotriazin-4(3H)-ones: A Metal-Free Approach

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8752 - 8756

Published: June 14, 2022

An efficient trifluoroacetic acid-mediated denitrogenative hydroxylation of 1,2,3-benzotriazin-4(3H)-ones is described. This metal-free approach compatible with a wide range 1,2,3-benzotriazin-4(3H)-ones, affording ortho-hydroxylated benzamides in good to high yields short reaction time. The believed proceed via benzene diazonium intermediate. synthetic utility the was successfully demonstrated by preparation an antimicrobial drug, Riparin C, and benzoxazine-2,4(3H)-diones yields.

Language: Английский

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Assembly of Benzo[c][1,2]dithiol-3-ones via Acid-Promoted Denitrogenative Transannulation of Benzotriazinones

Organic Letters, Journal Year: 2022, Volume and Issue: 24(49), P. 9012 - 9016

Published: Dec. 5, 2022

An expedient synthesis of benzo[c][1,2]dithiol-3-ones via metal-free denitrogenative transannulation benzotriazinones is developed, which represents the first example acid-mediated heteroannulation benzotriazinones. This newly discovered reactivity enables streamline diverse in decent yields by using sodium sulfide as sulfur source under simple reaction conditions.

Language: Английский

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Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(32)

Published: Aug. 23, 2023

Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.

Language: Английский

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Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

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