NDLI: One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines.

Please wait, while we are loading the content...

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines.

Content Provider	Europe PMC
Author	Tikhomolova, Alexandra S. Grinev, Vyacheslav S. Yegorova, Alevtina Yu.
Editor	Nenajdenko, Valentine G.
Copyright Year	2023
Abstract	We describe a method to synthesize a new class of hetarylaminomethylidene derivatives of furan-2(3H)-ones. The method uses 5-(4-chlorophenyl)furan-2(3H)-one, triethyl orthoformate, and heterocyclic amines with different ring sizes and heteroatoms under refluxing in absolute isopropyl alcohol. The obtained enamines exist in an equilibrium of E- and Z-isomers, whose configurations relative to the double exocyclic C=C bond were confirmed with a set of NMR spectroscopy data. The E-/Z-equilibrium of the synthesized compounds is affected by the configuration of the intermediate, the volume of its substituents, the site of enolate attack, the presence of intramolecular interactions of amino components, the time of the transformation, the order of mixing of the initial reagents, and the use of polar solvents in the NMR experiment. The advantages of the method are that the reaction time is short, the product yield is high, and product purification is easy.
Journal	Molecules
Volume Number	28
DOI	10.3390/molecules28030963
PubMed Central reference number	PMC9921198
Issue Number	3
PubMed reference number	36770633
e-ISSN	14203049
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2023-01-18
Access Restriction	Open
Subject Keyword	furan-2(3H)-ones hetarylaminomethylidene derivatives one-pot reactions selective synthesis physicochemical methods spectroscopy
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Hybrid hetarylhydrazones and enamines of Furan-2(3H)-ones as a framework for the synthesis of poly-N-heterocycles

Arylmethylene derivatives of 5-R-3H-furan-2-ones and N-aryl-5-R-3H-pyrrol-2-ones in reaction with acetylacetone

Reactions of 3-arylmethylene-3H-furan(pyrrol)-2-ones with azomethine ylide: synthesis of substituted azaspirononenes

Arylmethylidene derivatives of furan-2(3H)-ones in the synthesis of furopyridinecarbonitriles

Synthesis and primary cytotoxicity evaluation of arylmethylenenaphthofuranones derivatives

ZnO nanoparticle-catalyzed efficient one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones

3-Arylidene derivatives of 3H-furan-2-ones. Synthesis and reaction with maleic anhydride

Synthesis of 5-alkyl-3H-thiolen-2-ones and 5-alkyl-3H-furan-2-ones and condensation reactions at the heterocyclic methylene group

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines.

Similar Documents

Hybrid hetarylhydrazones and enamines of Furan-2(3H)-ones as a framework for the synthesis of poly-N-heterocycles

Arylmethylene derivatives of 5-R-3H-furan-2-ones and N-aryl-5-R-3H-pyrrol-2-ones in reaction with acetylacetone

Reactions of 3-arylmethylene-3H-furan(pyrrol)-2-ones with azomethine ylide: synthesis of substituted azaspirononenes

Arylmethylidene derivatives of furan-2(3H)-ones in the synthesis of furopyridinecarbonitriles

Synthesis and primary cytotoxicity evaluation of arylmethylenenaphthofuranones derivatives

ZnO nanoparticle-catalyzed efficient one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones

3-Arylidene derivatives of 3H-furan-2-ones. Synthesis and reaction with maleic anhydride

Synthesis of 5-alkyl-3H-thiolen-2-ones and 5-alkyl-3H-furan-2-ones and condensation reactions at the heterocyclic methylene group

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines.