19597-07-0Relevant articles and documents
MIXTURES OF ITACONIC ACID OR ITACONIC ACID DERIVATIVES AND PRIMARY AMINES FOR PRODUCING 1,3- AND 1,4-ALKYL METHYL PYRROLIDONES
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Page/Page column 13, (2011/10/19)
The present invention relates to a mixture comprising itaconic acid or an itaconic acid derivative and a primary amine of the formula (I) [in-line-formulae]R—NH2??(I)[/in-line-formulae] where the molar ratio of primary amine to itaconic acid or the itaconic acid derivative is in the range from 0.5:1 to 20:1, wherein the mixture comprises 50 mole percent or less of 4-carboxypyrrolidones of the formula (II), derivatives of the 4-carboxypyrrolidones of the formula (II) and 4-carbamidopyrrolidones of the formula (III) based on the itaconic acid used or the itaconic acid derivative used and in which R is a linear or branched saturated aliphatic radical having 1 to 24 carbon atoms or a saturated cycloaliphatic radical having 3 to 24 carbon atoms. The invention further provides for the use of the inventive mixtures for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones, and also a process for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones. In addition, the present invention relates to mixtures comprising 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones and 1,3-alkylmethylpyrrolidines, where the proportion of 1,3-alkylmethylpyrrolidines is in the range from 10 to 10 000 ppm, and to mixtures comprising 1,3-alkylmethylpyrrolidone and 1,4-alkylmethylpyrrolidone, wherein the molar ratio of 1,3-alkylmethylpyrrolidone to 1,4-alkylmethylpyrrolidone is in the range from 1:1 to 10:1.
Design, synthesis, and cyclization of 4-aminobutyric acid derivatives: Potential candidates as self-immolative spacers
Dewit, Matthew A.,Gillies, Elizabeth R.
experimental part, p. 1846 - 1854 (2011/05/03)
Self-immolative spacers have gained significant interest in recent years due to their utility in numerous prodrug, sensor and drug delivery systems. However, there are a very limited number of spacers that are capable of undergoing spontaneous and rapid reactions under mild conditions. To address this need, 4-aminobutyric acid derivatives were explored as a potential class of self-immolative spacers. Using a modular approach, eleven N- and α-substituted derivatives of 4-aminobutyric acid were synthesized, and their intramolecular cyclizations to γ-lactams were studied. Kinetics experiments were carried out at physiological pH and temperature, and the observed half-lives for the spacers ranged from 2 to 39 s, depending on the molecular structure. In addition, the pH dependence of the cyclization rate was also explored and it was found that cyclization still occurred rapidly at mildly acidic pH. Therefore, this class of compounds exhibits promise for incorporation into a variety of self-immolative systems where rapid cyclization reactions are desired.
A general and practical method of synthesis of 2-disubstituted-1- chloro- and 1-bromoenamines
Ghosez, Leon,George-Koch, Isabelle,Patiny, Luc,Houtekie, Marc,Bovy, Philippe,Nshimyumukiza, Prosper,Phan, Thao
, p. 9207 - 9222 (2007/10/03)
Disubstituted-α-chloroenamines are useful synthetic intermediates which had earlier been prepared by the reaction of tertiary amides with phosgene. The toxicity of the latter led us to systematically investigate new synthetic routes towards α-chloro- and
Preparation of Nitroalkenes: Substitution Reaction via Addition-Elimination Using β-Nitrovinyl Sulfoxides
Nobe, Manabu,Itoh, Akichika,Nishide, Kiyoharu,Abe, Hitoshi,Kawabata, Takeo,et al.
, p. 1119 - 1124 (2007/10/02)
Nitroalkenes were prepared by the substitution reaction of β-nitrovinyl sulfides and sulfoxides with a variety of carbon nucleophiles (i.e. alkylmetal reagents and enolates of carbonyl compounds), via an addition-elimination sequence.The sulfoxide as a leaving group was suitable for the reaction with an enolate of carbonyl compounds.This method was useful for the synthesis of nitroalkenes .
