16640-69-0Relevant articles and documents
A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters
Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 2099 - 2102 (2021/07/22)
A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of α-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl]2. Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.
Reductive Halogenation Reactions: Selective Synthesis of Unsymmetrical α-Haloketones
Lao, Zhiqi,Zhang, Huimiao,Toy, Patrick H.
supporting information, p. 8149 - 8152 (2019/10/21)
A method for the selective synthesis of unsymmetrical α-haloketones has been developed. The key transformation is a triphenylphosphine oxide catalyzed reductive halogenation of an α,β-unsaturated ketone in which trichlorosilane is the reducing reagent and an N-halosuccinimide is the electrophilic halogen source. This method allows for a halogen atom to be installed selectively at either of two very similarly substituted sites adjacent to a ketone group.
Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes
Aitken, David J.,Caboni, Pierluigi,Cuccu, Federico,Frongia, Angelo,Luridiana, Alberto,Secci, Francesco,Serusi, Lorenzo
supporting information, (2019/10/08)
An original tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides has been developed. Highly functionalized cyclopropanecarbaldehydes are obtained in good to high yield.
Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
Liu, Xiao-Dong,Ma, Hai-Yan,Xing, Chun-Hui,Lu, Long
, p. 1780 - 1783 (2017/07/27)
NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.
Synthesis and Biological Evaluation of Tricyclic Guanidine Analogues of Batzelladine K for Antimalarial, Antileishmanial, Antibacterial, Antifungal, and Anti-HIV Activities
Ahmed, Nafees,Brahmbhatt, Keyur G.,Khan, Shabana I.,Jacob, Melissa,Tekwani, Babu L.,Sabde, Sudeep,Mitra, Debashis,Singh, Inder P.,Khan, Ikhlas A.,Bhutani, Kamlesh K.
, p. 491 - 498 (2013/05/21)
Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (panel of bacteria and fungi), antiviral (HIV-1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine-sensitive D6 strain with IC50 1.25 and 0.88μm and chloroquine-resistant W2 strain with IC50 1.64 and 1.07μm, respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC50 2.39 and 2.78μm and IC90 11.27 and 12.76μm, respectively. Three analogues 12c, 14c, and 14i were the most active against various pathogenic bacteria and fungi with IC503.02μm and MIC/MBC/MFC 6μm. Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV-1. Our study demonstrated that the tricyclic guanidine compounds provide new structural class for broad spectrum activity. Fifty analogues of tricyclic guanidine derivative of batzelladine K were synthesized and tested for antimalarial, antileishmanial, antimicrobial, antifungal and anti-HIV activities. We have identified several active analogues.
Simple stereoselective synthesis of unsaturated lactone intermediates and their conversion into natural dihydropyranones and their enantiomers#
Shinde, Digambar Balaji,Kanth, Boddu Shashi,Satyakumar, Avula,Kamble,Das, Biswanath
, p. 317 - 323 (2013/07/26)
The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran-2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2-enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
IMPROVED PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND ANALOGUES THEREOF
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Page/Page column 13, (2010/11/03)
The present invention relates to an improved process for the preparation of prostaglandin and prostaglandin analogues, particularly PGF2α derivatives.
Antitumour polycyclic acridines. Part 13. Synthesis of 2-substituted 7H-pyrido[4,3,2-kl]acridines by thermolysis of 9-(5-alkyltriazol-1-yl)acridines
Ellis, Michael J.,Stevens, Malcolm F. G.
, p. 75 - 77 (2007/10/03)
Interaction of phosphoranylidene ketones with 9-azidoacridine in refluxing benzene affords 9-(5-substituted triazol-1-yl)acridines, which, on thermolysis in boiling diphenyl ether at 259 °C, yield 2-substituted 7H-pyrido[4,3,2-kl] acridines in high yields. These tetracyclic acridines are less potent inhibitors of human tumour cells in vitro than their pentacyclic analogues.
Charge-Directed Conjugate Addition Reactions in the Preparation of Substituted Methyl Ketones
Cooke, Manning P.,Burman, Diana L.
, p. 4955 - 4963 (2007/10/02)
Charge-directed conjugated addition reactions of the tert-butyl esters of α,β-unsaturated acylphosphoranes 2 have been used to prepare a variety of substituted methyl ketones.Substituted ylides 6 are prepared by alkylating ylide anions 4 generated by the addition of nucleophiles to 2 and are converted under acidic conditions to substituted (acylmethylene)phosphoranes 12 which are hydrolyzed to methyl ketones.The utility of these unsaturated acylphosphoranes as methyl vinyl ketone equivalents in conjugate addition-alkylation reactions is demonstrated in a synthesis of the racemic form of the sex pheromone of the California red scale, 14.
