14447-00-8Relevant academic research and scientific papers
Dialkylzinc-mediated atom transfer sequential radical addition cyclization
Feray, Laurence,Bertrand, Michele P.
, p. 3164 - 3170 (2008)
Alkylative cycloisomerization of N,N-diallylpropiolamide into α-alkylidene-γ-lactams was mediated by dialkylzinc reagents in aerobic medium. In the presence of an alkyl iodide, final oxidation by iodine-atom transfer predominates over reductive zincation. The dialkylzinc-mediated radical process tolerates the presence of the acidic terminal alkyne. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
Aleksi?, Jovana,Stojanovi?, Milovan,Baranac-Stojanovi?, Marija
, p. 1811 - 1835 (2018/07/29)
We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope a
A Novel Regio- and Stereospecific Hydrohalogenation Reaction of 2-Propynoic Acid and Its Derivatives
Ma, Shengming,Lu, Xiyan,Li, Zhigang
, p. 709 - 713 (2007/10/02)
2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products.A rationale for the regio- and stereospecifity is briefly discussed.
INTRAMOLECULAR CYCLIZATION OF ALLYLIC PROPIOLATES MEDIATED BY THE ADDITION OF STANNYL RADICALS: A NEW SYNTHETIC ROUTE TO α-METHYLENE-γ-BUTYROLACTONES
Lee, Eun,Ko, Sung Bo,Jung, Kyung Woon,Chang, Moon Ho
, p. 827 - 828 (2007/10/02)
Allylic propiolates react with tributyl- or triphenylstannane to yield α-(stannyl)methylene-γ-butyrolactones. α-Methylene-γ-butyrolactones are easily prepared by destannylation.
IMPROVED PREPARATION OF ALIPHATIC PROPYNOIC ESTERS
Balas, L.,Jousseaume, B.,Langwost, B.
, p. 4525 - 4526 (2007/10/02)
An improved procedure of esterification of propynoic acid, based on the N,N'-dicyclohexylcarbodiimide 4-dimethylaminopyridine condensation, is presented, which gives good results with primary, secondary, allylic and homoallylic alcohols.Reactions conditions are mild.Some limitations are given.
1,3-Dipolar Cycloadditions of Nitrones Derived from the Reaction of Acetylenes with Hydroxylamines
Padwa, Albert,Wong, George S. K.
, p. 3125 - 3133 (2007/10/02)
A study of the reaction of hydroxylamines with a variety of acetylenes has been carried out.Methylhydroxylamine readily reacts with methyl propiolate to give methyl 4-carbomethoxy-2-methyl-4-isoxazolidine-3-acetate.Further heating of this material results
