Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1508 - 1521

Published: April 8, 2022

Abstract Enaminones have in the past decade received renewed interest organic synthesis by acting as highly versatile building blocks. Particularly, featured amino and carbonyl group enaminone structure endow them with ability of tolerating water via hydrogen bonding effect. Thus, designing synthetic methods aqueous medium enaminones main blocks has extensive attention notable success. Based on our longstanding efforts interests chemistry, we review herein research advances participated medium. magnified image

Language: Английский

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Recent advances in transition metal-free annulation toward heterocycle diversity based on the C–N bond cleavage of enaminone platform

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2356 - 2369

Published: Jan. 1, 2022

Enaminones and analogous stable enamines are well known as platform building blocks in organic synthesis for the construction of heterocyclic compounds, especially N-heterocycles. To date, enaminones have been successfully employed various 5- or 6- membered heterocycles. Recently, synthetic protocols accomplished by diversity-oriented annulation reactions based on C-N bond cleavage gained notable success. In this review, development transition metal-free product featuring a is reviewed.

Language: Английский

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Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

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Copper-catalyzed C–H/N–H annulation of enaminones and alkynyl esters for densely substituted pyrrole synthesis

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(11), P. 1808 - 1811

Published: Jan. 1, 2022

Herein, the copper-catalyzed annulation of enaminones with alkynyl esters for facile synthesis different pyrroles a 2,3,4,5-tetrasubstituted structure has been developed. With Cu(OAc)2 as only catalyst, tunable 2-vinyl and 2,3-dicarboxyl-functionalized achieved by using terminal internal esters, respectively. The represents first example accessing substituted via direct cascade reactions involving vinylation pyrrole ring formation.

Language: Английский

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“Alkene-to-Alkene” Difunctionalization of Enaminones for the Synthesis of Polyfunctionalized Alkenes by Transition-Metal-Free C–H and C–N Bond Transformation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8451 - 8456

Published: Nov. 16, 2023

The three-component reactions of enaminones, disulfides, and alcohols for the synthesis polyfunctionalized alkenes have been realized via C-H C-N bond transformation on enaminones. proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. application alkene products divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, isoxazoles, simple annulation has also verified.

Language: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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Ultrasound-Promoted Synthesis of α-Thiocyanoketones via Enaminone C═C Bond Cleavage and Tunable One-Pot Access to 4-Aryl-2-aminothiazoles

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8248 - 8255

Published: May 26, 2022

Ultrasound has been successfully employed to promote the thiocyanation of C═C bond in enaminones for synthesis α-thiocyanoketones and 2-aminothiazoles. The reactions with ammonium thiocyanate provide ultrasound irradiation at room temperature. More interestingly, simply further heating vessel after ultrasonic leads selective 2-aminothiazoles an unconventional 4-aryl substructure.

Language: Английский

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Unlock the C–N Bond Amidation of Enaminones: Metal-Free Synthesis of Enamides by Water-Assisted Transamidation

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 216 - 223

Published: Dec. 18, 2023

The C–N bond transamidation of primary amides with N,N-dimethyl enaminones has been efficiently realized by heating in the presence trifluoromethanesulfonic acid (TfOH). method enables practical synthesis valuable enamides without use any metal reagent. In addition, this protocol can also be expanded to reactions sulfonamides, and late-stage functionalization on sulfonamide drugs such as Celecoxib Valdecoxib verified. Moreover, participation water assisting process identified isotope labeling experiments using D2O, disclosing a new possibility designing catalytic tactic other reactions.

Language: Английский

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Nickel-Catalyzed Reductive Borylation of Enaminones via C(sp²)–N Bond Cleavage

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 10349 - 10358

Published: July 27, 2022

The cleavage and transformation of alkenyl C(sp2)-N bonds is a significant synthetic challenge. Herein we described an unprecedented nickel-catalyzed reductive borylation enaminones to synthesize β-ketone boronic esters. Notably, B2pin2 played the dual role in this process, water served as hydrogen source, which was transferred target products. air-stable nickel catalyst applied bonds, concomitant with process ester intermediates, on basis mechanism study.

Language: Английский

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