77547-07-0Relevant academic research and scientific papers
A new synthesis of exo-methylene butyrolactones from nitroalkanes
Ballini,Bosica,Livi
, p. 1519 - 1522 (2001)
A versatile route to exo-methylene butyrolactones was developed by employing a three step reaction sequence consisting of Michael addition of primary nitroalkanes 1 to ethyl (2-bromomethyl) acrylate (2), then Nef conversion of the nitro derivatives 3, and subsequent lactonization of the obtained keto esters 4. The method is chemoselective for important functionalities such as ester, C=C double bond and hydroxyl.
New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
Jun-Tao, Feng,De-Long, Wang,Yong-Ling, Wu,He, Yan,Xing, Zhang
, p. 4393 - 4397 (2013/07/26)
Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the α-methylene-γ-butyrolactone ring, a natural pharmacophore. All structures were confirmed by 1H and 13C NMR, MS, and single-c
Novel synthesis, cytotoxic evaluation, and structure-activity relationship studies of a series of α-alkylidene-γ-lactones and lactams
Janecki, Tomasz,B?aszczyk, Edyta,Studzian, Kazimierz,Janecka, Anna,Krajewska, Urszula,Rózalski, Marek
, p. 3516 - 3521 (2007/10/03)
5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a-e, 3-alkylidenedihydrofuran-2-ones 18a-c, and 3-methylenepyrrolidin-2-ones 16a-e were synthesized utilizing ethyl 2-diethoxyphosphoryl-4-nitroalkanoates 9a-e as common intermediates. All obtained
2-Diethoxyphosphoryl-4-nitroalkanoates - Versatile intermediates in the synthesis of α-alkylidene-γ-lactones and lactams
B?aszczyk, Edyta,Krawczyk, Henryk,Janecki, Tomasz
, p. 2685 - 2688 (2007/10/03)
Michael addition of various nitroalkanes 7a-f to ethyl (2- diethoxyphosphoryl)acrylate (6) gave 2-diethoxyphosphoryl-4-nitroalkanoates 8a-f. Transformation of the nitro functionality into hydroxy or amino group and cyclization yielded 3-(diethoxyphosphory
A New Synthesis of γ-Substituted α-Methylene-γ-butyrolactones (2-Methylene-4-alkanolides) using Catalysis by SnCl2/Amberlyst 15
Talaga, Patrice,Schaeffer, Marcel,Benezra, Claude,Stampf, Jean-Luc
, p. 530 (2007/10/02)
Reaction of α-bromomethylacrylic acid with aldehydes or ketones in an SnCl2/amberlyst 15/THF/H2O system affords 2-methylene-4-alkanolides in mostly good yields.
An SnCl2-Promoted α-Methylene-γ-butirolactone Synthesis in an Aqueous Medium
Uneyema, Kenji,Ueda, Kunimasa,Torii, Sigeru
, p. 1201 - 1202 (2007/10/02)
Reaction of α-bromomethylacrylic acid with aldehydes in an SnCl2-MeOCH2CH2OH-H2O system provides γ-substituted-α-methylene-γ-butirolactones.
REFORMATSKY-TYPE REACTIONS IN AQUEOUS MEDIA. USE OF BROMOMETHYLACRYLIC ACID FOR THE SYNTHESIS OF α-METHYLENE-γ-BUTYROLACTONES.
Mattes, Henri,Benezra, Claude
, p. 5697 - 5698 (2007/10/02)
A new method for the preparation of α-methylene-γ-butyrolactones is described.
