91230-06-7Relevant academic research and scientific papers
Ruthenium-catalyzed alkene-alkyne coupling of disubstituted olefins: Application to the stereoselective synthesis of trisubstituted enecarbamates
Trost, Barry M.,Cregg, James J.
, p. 620 - 623 (2015)
The Ru-catalyzed alkene-alkyne coupling reaction has been demonstrated to be an enabling methodology for the synthesis of complex molecules. However, to date, it has been limited to monosubstituted olefins. Herein we report the first general utilization o
N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate
Van Veen, Branca C.,Wales, Steven M.,Clayden, Jonathan
, p. 8538 - 8543 (2021/06/30)
We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability.
Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine
Legnani, Luca,Morandi, Bill
supporting information, p. 2248 - 2251 (2016/02/18)
Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.
4,5-DIHYDROISOXAZOLE DERIVATIVES AS NAMPT INHIBITORS
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Page/Page column 29; 31, (2014/08/06)
The present invention provides substituted 4,5-dihydroisoxazole derivatives of formula (I), which may be therapeutically useful, more particularly NAMPT inhibitors and in which R1 R2, Y, X, "Het" and "p" have the meanings given in the specification, and pharmaceutically acceptable salts thereof that are useful in the treatment and prevention of diseases or disorder caused by an elevated level of nicotinamide phosphoribosyltransferase (NAMPT) in a mammal. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of the substituted 4,5-dihydroisoxazole derivatives of formula (I) or a pharmaceutically acceptable salts or stereoisomers or N-oxide thereof.
Total synthesis of pulchellalactam via an RCM strategy
Chavan, Subhash P.,Pathak, Ashok B.,Dhawane, Abasaheb N.,Kalkote
, p. 1503 - 1510 (2008/02/03)
Total synthesis of (Z) pulchellalactam, a CD protein tyrosine phosphatase inhibitor, from commercially available methallyl chloride employing ring-closure metathesis (RCM) as a key step is described. Copyright Taylor & Francis Group, LLC.
N-silyl-tethered radical cyclizations: a new synthesis of gamma-amino alcohols.
Blaszykowski, Christophe,Dhimane, Anne-Lise,Fensterbank, Louis,Malacria, Max
, p. 1341 - 1344 (2007/10/03)
[reaction: see text] Various allylic and propargylic amines bearing a protecting group (PG) have been employed in N-silyl-tethered radical cyclizations. The resulting silapyrrolidine adducts could be smoothly oxidized, creating access to gamma-amino alcoh
Ring closing metathesis of phenyl-substituted dienes
Bujard,Briot,Gouverneur,Mioskowski
, p. 8785 - 8788 (2007/10/03)
A series of phenyl-substituted heterodienes 2a-f and 6 was prepared and subjected to ring closing metathesis (RCM) to give differently phenyl- substituted dihydropyrroles and dihydrofuran.
Phosphinic acid analogues of GABA. 2. Selective, orally active GABA(B) antagonists
Froestl,Mickel,Von Sprecher,Diel,Hall,Maier,Strub,Melillo,Baumann,Bernasconi,Gentsch,Hauser,Jaekel,Karlsson,Klebs,Maitre,Marescaux,Pozza,Schmutz,et al.
, p. 3313 - 3331 (2007/10/02)
In 1987, 25 years after the synthesis of the potent and selective GABA(B) agonist baclofen (1), Kerr et al. described the first GABA(B) antagonist phaclofen 2. However, phaclofen and structurally similar derivatives 3-5 did not cross the blood-brain barrier and hence were inactive in vivo as central nervous system agents. As a consequence, the therapeutic potential of GABA(B) antagonists remained unclear. In exploring GABA and baclofen derivatives by replacing the carboxylic acid residue with various phosphinic acid groups, we discovered more potent and water soluble GABA(B) antagonists. Electrophysiological experiments in vivo demonstrated that some of the new compounds were capable of penetrating the blood-brain barrier after oral administration. Neurotransmitter release experiments showed that they interacted with several presynaptic GABA(B) receptor subtypes, enhancing the release of GABA, glutamate, aspartate, and somatostatin. The new GABA(B) antagonists interacted also with postsynaptic GABA(B) receptors, as they blocked late inhibitory postsynaptic potentials. They facilitated the induction of long-term potentiation in vitro and in vivo, suggesting potential cognition enhancing effects. Fifteen compounds were investigated in various memory and learning paradigms in rodents. Although several compounds were found to be active, only 10 reversed the age-related deficits of old rats in a multiple-trial one-way active avoidance test after chronic treatment. The cognition facilitating effects of 10 were confirmed in learning experiments in Rhesus monkeys. The novel GABA(B) antagonists showed also protective effects in various animal models of absence epilepsy.
Electrophilic amination of carbanions with metallated t-butyl N-tosyloxycarbamate
Greck, Christine,Bischoff, Laurent,Girard, Anne,Hajicek, Josef,Genet, Jean-Pierre
, p. 429 - 433 (2007/10/02)
The reactivity of metallated t-butyl N-tosyloxycarbamate as electrophilic aminating reagent was studied.N-Boc-protected primary alkyl and aryl amines were obtained by reaction of organometallic derivatives with this reagent. - Keywords: electrophilic amin
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
