3695-90-7Relevant articles and documents
Enantioselective ene-reduction of E-2-cyano-3-(furan-2-yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)-2-cyano-3-(furan-2-yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra
Jimenez, David E.Q.,Barreiro, Juliana C.,dos Santos, Fernando M.,de Vasconcellos, Suzan P.,Porto, André L.M.,Batista, Jo?o M.
, p. 534 - 542 (2019)
This work reports the green organic chemistry synthesis of E-2-cyano-3(furan-2-yl) acrylamide under microwave radiation (55?W), as well as the use of filamentous marine and terrestrial-derived fungi, in the first ene-reduction of 2-cyano-3-(furan-2-yl) acrylamide to (R)-2-cyano-3-(furan-2-yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN-bearing stereogenic center at the α-C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)-2-cyano-3-(furan-2-yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2-cyano-3-(furan-2-yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents.
Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
Rupanawar, Bapurao D.,Veetil, Sruthi M.,Suryavanshi, Gurunath
, p. 6232 - 6239 (2019/11/05)
Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.
An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction
Narendar Reddy, Thatikonda,Raktani, Bikshapathi,Perla, Ramesh,Ravinder, Mettu,Vaidya, Jayathirtha Rao,Babu, N. Jagadeesh
, p. 9203 - 9209 (2017/08/29)
Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.