32727-94-9Relevant academic research and scientific papers
A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester
Nizovtsev, Alexey V.,Bovin, Nicolai V.
supporting information, p. 4428 - 4432 (2021/08/20)
A new convenient synthetic route to 2-aminopropane-1,2,3-tricarboxylic acid is described. The first two stages of the threestep synthesis are performed in a one-pot procedure and include the cyclization of hippuric acid with DCC followed by treatment with methyl bromoacetate to yield an alkylated oxazolone. Its hydrolysis with HCl provides 2-aminopropane-1,2,3-tricarboxylic acid as its HCl salt. Esterification of the resulting acid with methanol in the presence of thionyl chloride leads selectively to its symmetrical diester.
Investigation of the pyridinium ylide-alkyne cycloaddition as a fluorogenic coupling reaction
Bonte, Simon,Ghinea, Ioana Otilia,Dinica, Rodica,Baussanne, Isabelle,Demeunynck, Martine
supporting information, (2016/04/20)
The cycloaddition of pyridinium ylides with alkynes was investigated under mild conditions. A series of 13 pyridinium salts was prepared by alkylation of 4-substituted pyridines. Their reactivity with propiolic ester or amide in various reaction conditions (different temperatures, solvents, added bases) was studied, and 11 indolizines, with three points of structural variation, were, thus, isolated and characterized. The highest yields were obtained when electron-withdrawing groups were present on both the pyridinium ylide, generated in situ from the corresponding pyridinium salt, and the alkyne (X, Z = ester, amide, CN, carbonyl, etc.). Electron-withdrawing substituents, lowering the acid dissociation constant (pKa) of the pyridinium salts, allow the cycloaddition to proceed at pH 7.5 in aqueous buffers at room temperature.
Synthesis of 2-aminoindolizines by 1,3-dipolar cycloaddition of pyridinium ylides with electron-deficient ynamides
Brioche, Julien,Meyer, Christophe,Cossy, Janine
supporting information, p. 2800 - 2803 (2015/06/16)
Electron-deficient ynamides, possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.
Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage
Zhao, Baoli
supporting information; experimental part, p. 7108 - 7119 (2012/09/25)
New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc) 2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.
Design, Synthesis, and Biological Evaluation of 6-Substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: A Novel Class of Diarylheterocyclic Selective Cyclooxygenase-2 Inhibitors
Rao, P.N. Praveen,Amini, Mohsen,Li, Huiying,Habeeb, Amgad G.,Knaus, Edward E.
, p. 4872 - 4882 (2007/10/03)
A group of 6-alkyl (alkoxy or alkylthio)-4-aryl-3-(4-methanesulfonylphenyl)pyran-2-ones (14a-v), possessing either a H or F substituent at the para-position of the C-4 phenyl ring, were designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibit
Preparation of 1-trifluoroacetyl indolizines and their derivatives via the cycloaddition of pyridinium N-ylides with 4-4-ethoxy1-1,1,1-trifluorobut-3-en-one
Zhu, Shi-Zheng,Qin, Chao-Yue,Wang, Yan-Li,Chu, Qian-Li
, p. 183 - 187 (2007/10/03)
Under basic reaction conditions pyridinium or isoquinolinium N-ylides (C5H5N+ CH2YBr- or C9H7N+CH2YBr-, Y : CO2R, CN, PhCO) reacted readily with 4-ethoxyl-1,1,1-trifluorobut-3-en-2-one to give the corresponding 1-trifluoroacetyl substituted indolizines or pyrrolo-[1,2-a]isoquinolines. The molecular structure of 1-trifluoromethyl-3-methoxyl-pyrrolo-[1,2-a]isoquinoline is presented.
Reaction of N-alkylpyredinium salts with phosphorus trichloride
Bansal, Raj K.,Gupta, Neelima,Gupta, Rakhi,Pandey, Garima,Agarwal, Mamta
, p. 121 - 130 (2007/10/03)
1-Alkylpyridinium bromides 1 having activated N-methylene group react with phosphorus trichloride to give N-(dichlorophosphinomethylene)pyridinium ylides 2. The site of the reaction in 1,2-dialkylpyridinium halides 3 under these conditions is determined by the relative activation of 1- and 2-methylene groups; in the absence of sufficient activation of N-methylene group, reaction occurs at the 2-methylene group to give dichlorophosphinylated anhydrobases 5 and 11. 1,4-Dialkylpyridinium bromide 13 behaves analogously to give the corresponding dichlorophosphinylated anhydrobase 14.
FLUOROCARBON DERIVATIVES OF NITROGEN. PART 19. SYNTHESIS AND MASS SPECTROMETRIC ANALYSIS OF SOME PYRIDINIUM (TETRAFLUORO-4-PYRIDYL)METHYLIDES
Banks, Ronald Eric,Flowers, William Thain,Khaffaf, Suad Najmaldin
, p. 127 - 142 (2007/10/02)
Nine new pyridinium methylides have been synthesised via SNAr displacement of the 4-fluorine from pentafluoropyridine with pyridinium phenacylide py+-C-(COPh)C5F4N-4> and a range of pyridium alkoxycarbonylmethylides
Pyridinium aryl hydrazide compounds
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, (2008/06/13)
Photographic silver halide elements containing aryl hydrazides as defined for the production of images with ultrahigh contrast and a new class of aryl hydrazides with a cationic group in the aryl radical as defined. The photographic silver halide elements can be developed at relatively low pH values and have low fog and low tendency to form black spots in unexposed or slightly exposed areas.
