34085-09-1Relevant academic research and scientific papers
Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950
Coleman, Robert S.,Liu, Pei-Hua
, p. 577 - 580 (2004)
(Matrix presented) A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)-and (Z)-vinyl iodides with a protected maleimide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.
Dimethyldioxirane oxidation of 2-silyloxypyrroles: An efficient regiocontrolled synthesis of 5-hydroxy-3-pyrrolin-2-ones
Boukouvalas, John,Xiao, Yufang,Cheng, Yun-Xing,Loach, Richard P.
, p. 3198 - 3200 (2008/09/20)
A new method for the synthesis of 5-hydroxy-3-pyrrolin-2-ones is reported. Conversion of N-Boc-3-pyrrolin-2-ones into 2-triisopropylsilyloxypyrroles and ensuing oxidation with dimethyldioxirane provides the corresponding N-Boc-5-hydroxy-3-pyrrolin-2-ones in high yields. Georg Thieme Verlag Stuttgart.
Regioselective reduction of maleimide and citraconimide derivatives: General preparation of 5-hydroxy-1,5-dihydropyrrol-2-one
Mase, Nobuyuki,Nishi, Toshiki,Hiyoshi, Masaomi,Ichihara, Kazuhiro,Bessho, Junichiro,Yoda, Hidemi,Takabe, Kunihiko
, p. 707 - 709 (2007/10/03)
NaBH4 reduction of citraconimide derivatives regioselectively afforded 5-hydroxy-4-methyl-1,5-dihydropyrrol-2-ones, whereas NaBH4-CeCl3 or DIBAL-H reduction gave 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-ones.
Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using Candida antarctica Lipase B: Synthetic and Structural Aspects
Cuiper, Agnes D.,Kouwijzer, Milou L. C. E.,Grootenhuis, Peter D. J.,Kellogg, Richard M.,Feringa, Ben L.
, p. 9529 - 9537 (2007/10/03)
Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterification. N-Acyl-5-(acyloxy)pyrrolinones 1 (R2 = acyl) are synthesized by applying this method with 100% yield and >99% ee. To rationalize the observed enantioselectivity and the substituent effects of these reactions both empirical models and molecular modeling studies have been used, and a qualitative agreement was found between the results from these studies and the experimental results.
2-Aza-2,4-cyclopentadione. Existence and Reactivity
Gavina, F.,Costero, A. M.,Andreu, M.R.,Carda, M.,Luis, S.V.
, p. 4017 - 4018 (2007/10/02)
The elusive species 2-aza-2,4-cyclopentadienone has been generated from an insoluble polymeric precursor.The liberated intermediate can act either as diene or as a dienophile in Diels-Alder reactions.
ISOLATION AND CHARACTERIZATION OF DIHYDROMALEIMIDE AND ITS GLUCOSIDE AS GROWTH INHIBITORS FROM DWARF PEA
Masuko, Michio,Miyamoto, Kensuke,Sakurai, Kensuke,Iino, Moritoshi,Takeuchi, Yasuyoshi,Hashimoto, Tohru
, p. 1278 - 1280 (2007/10/02)
Two new growth inhibitors , R-dihydromaleimide and R-dihydromaleimide β-D-glucoside, were isolated from 2-week-old pea shoots.- Key Words: Pisum sativum; Leguminosae; dwarf pea; growth inhibitor; R-dihydromaleimide; R-dihydromaleimide-β-D-glucoside.
SYNTHESIS OF 5-HYDROXY-3-METHYL-3-PYRROLIN-2-ONE AND ITS 4-METHYL ISOMER
Nagasaka, Tatsuo,Esumi, Sayuri,Ozawa, Naganori,Kosugi, Yoshiyuki,Hamaguchi, Fumiko
, p. 1987 - 1992 (2007/10/02)
5-Hydroxy-3-methyl-3-pyrrolin-2-one (1), which is known as jatropham; an antitumor alkaloid, is conveniently synthesized from succinimide.One step synthesis of 5-hydroxy-4-methyl-3-pyrrolin-2-one (2) by the regioselective reduction of methylmaleimide with NaBH4/H+ is also described.
