NDLI: Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

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

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

Content Provider	Scilit
Author	Trofimov, Boris A. Malkina, Anastasiya G. Stepanov, Anton V. Sobenina, Lyubov N. Shemyakina, Olesya A. Ushakov, Igor A. Smirnov, Vladimir I.
Copyright Year	2016
Description	It is shown for the first time that the reaction of cyanopropargylic alcohols with carboxylic acids in the presence of triethylamine (5–100 mol%) under microwave irradiation (MeCN, 100 °C, 1.2 atm) follows two competing pathways to afford 4-cyano-3(2H)-furanones (1:1 adduct) and 4-cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans (2:1 adduct) in moderate to good yields. The ratio of the products depends on both the reaction conditions (the reactant ratio, catalyst content) and the reactant structure, the 2:1 adduct formation being favored by an excess of cyanopropargylic alcohol, lower catalyst content, and bulky substituents at the carboxylic functions. Both competing reactions proceed via the same intermediates, keto esters, which either intramolecularly cyclize to the 1:1 adducts, or intermolecularly add the second molecule of cyanopropargylic alcohol to give the 2:1 adducts.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561591.pdf
Ending Page	1891
Page Count	12
Starting Page	1880
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-0035-1561591
Journal	Synthesis
Issue Number	12
Volume Number	48
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2016-04-14
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Cyanopropargylic Alcohols Nucleophilic Addition 3-dihydrofuran Derivatives
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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

Synthesis of 5-Thienylfuran-3(2H)-ones via the Microwave-Assisted Tandem Reaction of Cyanopropargylic Alcohols with Thiophene-2-carboxylic Acids

A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)-Furanone Moieties

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

A Convenient Synthetic Method for β-Alkoxy- and β-Phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids

Chemo- and regioselective modification of l-histidine with tertiary cyanopropargylic alcohols

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction

Synthesis of New Pyridazinone Derivatives: 2,6-Disubstituted 5-Hydroxy-3(2H)-pyridazinone-4-carboxylic Acid Ethyl Esters

Microwave-Assisted Copper-Powder-Catalyzed Coupling and Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids with 1,3-Diketones Leading to 2H-Pyran-2-ones

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

Similar Documents

Synthesis of 5-Thienylfuran-3(2H)-ones via the Microwave-Assisted Tandem Reaction of Cyanopropargylic Alcohols with Thiophene-2-carboxylic Acids

A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)-Furanone Moieties

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

A Convenient Synthetic Method for β-Alkoxy- and β-Phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids

Chemo- and regioselective modification of l-histidine with tertiary cyanopropargylic alcohols

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction

Synthesis of New Pyridazinone Derivatives: 2,6-Disubstituted 5-Hydroxy-3(2H)-pyridazinone-4-carboxylic Acid Ethyl Esters

Microwave-Assisted Copper-Powder-Catalyzed Coupling and Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids with 1,3-Diketones Leading to 2H-Pyran-2-ones

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydro­furans

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans