- Process for preparing azelaic acid
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A process for preparing azelaic acid is disclosed. In particular, the process for preparing azelaic acid is an ozone free process. The process for preparing azelaic acid comprises a step of decarboxylation of tetra-carboxylic acid in the presence of a organic sulfonic acid.
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Paragraph 0096; 0097
(2021/02/19)
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- Rapid radiosynthesis of [11C] and [14C]azelaic, suberic, and sebacic acids for in vivo mechanistic studies of systemic acquired resistance in plants
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A recent report that the aliphatic dicarboxylic acid, azelaic acid (1,9-nonanedioic acid) but not related acids, suberic acid (1,8-octanedioic acid) or sebacic (1,10-decanedioic acid) acid induces systemic acquired resistance to invading pathogens in plants stimulated the development of a rapid method for labeling these dicarboxylic acids with 11C and 14C for in vivo mechanistic studies in whole plants. 11C-labeling was performed by reaction of ammonium [ 11C]cyanide with the corresponding bromonitrile precursor followed by hydrolysis with aqueous sodium hydroxide solution. Total synthesis time was 60min. Median decay-corrected radiochemical yield for [11C]azelaic acid was 40% relative to trapped [11C]cyanide, and specific activity was 15GBq/μmol. Yields for [11C]suberic and sebacic acids were similar. The 14C-labeled version of azelaic acid was prepared from potassium [14C]cyanide in 45% overall radiochemical yield. Radiolabeling procedures were verified using 13C-labeling coupled with 13C-NMR and liquid chromatography-mass spectrometry analysis. The 11C and 14C-labeled azelaic acid and related dicarboxylic acids are expected to be of value in understanding the mode-of-action, transport, and fate of this putative signaling molecule in plants.
- Best, Marcel,Gifford, Andrew N.,Kim, Sung Won,Babst, Ben,Piel, Markus,Roesch, Frank,Fowler, Joanna S.
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experimental part
p. 39 - 43
(2012/06/29)
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- Applications of surfactant-modified clays to synthetic organic chemistry
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Two triphase catalysts (SLL) have been developed for organic phase-aqueous phase reactions catalyzed by suitable modified clay (solid phase). These triphase catalysts have been applied to nucleophilic displacement on activated (benzylic) as well as unactivated organic halides and provide a convenient and effective method of preparation of the corresponding products. Other useful transformations to, which these triphase catalysts have been successfully applied are the synthesis of 9,9-dichloro bicyclo[6.1.0]nonane, O-alkylation and C-alkylation of β-naphthol.
- Ghiaci,Sedaghat,Kalbasi,Abbaspur
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p. 5529 - 5534
(2007/10/03)
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- Orthocarbonsaeure-ester mit 2,4,10-Trioxaadamantanstruktur als Carboxylschutzgruppe; Verwendung zur Synthese von substituierten Carbonsaeuren mit Hilfe von Grignard-Reagenzien
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The surprising stability of 2,4,10-trioxa-3-adamantyl derivatives 1 against nucleophilic substitution by organomagnesium compounds is discussed and shown to be caused by unfavourable stereoelectronic and steric factors governing the substitution of these cage compounds (Scheme 2).As a consequence, a number of Grignard reagents 2 containing the carboxyl group masked as 2,4,10-trioxa-3-adamantyl group could be prepared and have been reacted in a second step with various electrophiles (cf.Scheme 4).In the products 7-13 and 15b the carboxyl masking group is removed by mild ac id hydrolysis and saponification (cf.Scheme 3) to yield the corresponding acids 16a-21a, 22, and 23a.Acids 21a and 23a have been further transformed to give the macrocyclic lactones 24 and 26, isolated from Galbanum oleo-gum-resin, and acid 22 to give 12-methyl-13-tridecanolide (25), isolated from Angelica root oil.In addition 1-bromo-ω-(2,4,10-trioxa-3-adamantyl)alkanes 1c and 1b have been used to synthesize (+/-)-methyl recifeiolate (29b) and pure cis-ambrettolic acid ((Z)-32a).
- Voss, Gundula,Gerlach, Hans
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p. 2294 - 2307
(2007/10/02)
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- A simple approach to 12-azaprostaglandin congeners
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The base-catalysed alkylation of N-acylated 3-pyrrolines has been studied.The reaction has been utilized in an approach to the synthesis of 12-azaprostaglandins according to the following sequence. 3-Pyrroline was acylated with 1-chloro-1-octen-3-one and the resulting amide alkylated at the 2-position with I-(CH2)6C(OCH3)3.Subsequently, the α- and β-(13,14-dihydro)-prostanoid chains were formed by sodium borohyride reduction, followed by hydrolysis.The resulting product, 1-(3-hydroxyoctyl)-2-(6-methoxycarbonylhexyl)-3-pyrroline (13), constitutes a central intermediate for 12-azaprostaglandins.
- Armande, J. C. Lapierre,Pandit, U. K.
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