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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Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(13), P. 5058 - 5063

Published: Jan. 1, 2022

The electrochemical annulation of enaminones/analogous enamines and thioureas providing 2-aminothiazoles has been realized. Modulating the electrolyte enables diastereoselective synthesis 4,5-dialkoxyl thiazolines by dearomatization.

Language: Английский

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Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF₂CO₂Et toward 2,2-Difluorinated 2,3-Dihydrofurans

Organic Letters, Journal Year: 2022, Volume and Issue: 24(12), P. 2404 - 2408

Published: March 18, 2022

A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via [4 + 1] annulation enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent enables annulative difluoromethylation by partial cleavage C═C double bond. In addition, further treatment hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) a formal enaminone C-N carboxylation.

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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Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4833 - 4838

Published: March 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

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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Recent developments in the synthesis of nitrogen-containing heterocycles from β-aminovinyl esters/ketones as CC–N donors

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 20(2), P. 282 - 295

Published: Nov. 19, 2021

The synthesis of nitrogen-containing heterocycles from β-aminovinyl esters(ketones) was reviewed according to the classification final heterocycle synthesis.

Language: Английский

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Photocatalytic Transition‐Metal‐Free Direct 3‐Acetalation of Quinoxaline‐2(1H)‐ones

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(22), P. 2655 - 2662

Published: Aug. 16, 2022

Comprehensive Summary A general transition‐metal‐free visible‐light‐promoted 3‐acetalation reaction of quinoxaline‐2(1 H )‐ones was developed under mild conditions. By employing 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as an inexpensive photocatalyst, and glyoxylic acid acetal a radical source, various acetalated were constructed in moderate to good yields. Moreover, the versatility this protocol is highlighted by successful application late‐stage modification drug molecules functionality transformations. The excellent antitumor activity product demonstrated that streamlined sustainable approach could have emerged powerful strategy for structural medicinal chemistry.

Language: Английский

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Nickel‐Catalyzed Tandem Ring Contraction of TEMPO and C−N Bond Transamination of Enaminones toward Amino Diversity of Enaminones

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(26)

Published: June 22, 2022

Abstract The reactions of N,N ‐substituted enaminones with TEMPO leading to the synthesis 2,2‐dimethyl pyrrolidine functionalized new have been established by Ni(II) catalysis. interesting ring contraction on as well enaminone C−N bond amination bring tool for generating molecular diversity in amino group fragment.

Language: Английский

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