129319-91-1Relevant academic research and scientific papers
Protected Chloroethyl and Chloropropyl Amines as Conformationally Unrestricted Annulating Reagents
Shi, Qing,Meehan, Mariah C.,Galella, Michael,Park, Hyunsoo,Khandelwal, Purnima,Hynes, John,Dhar, T. G. Murali,Marcoux, David
supporting information, p. 337 - 340 (2018/01/28)
The purpose of this letter is to document the use of protected chloroethyl and chloropropyl amines as conformationally unrestricted ambiphilic reagents that undergo annulation reactions with Michael acceptors. This reaction is wide in scope and utilizes r
Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues
Bringmann, Gerhard,Gulder, Tanja,Hertlein, Barbara,Hemberger, Yasmin,Meyer, Frank
scheme or table, p. 1151 - 1158 (2010/04/01)
The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids will now facilitate the preparation of structural analogues for structure-activity relationship studies. Its general applicability was shown by the preparation of the sterically even more congested, as yet unnatural N,3′- and N,1′-coupled analogues, ancistrocladinium C (5) and D (6).
NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
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Page/Page column 40, (2009/10/06)
Disclosed herein are compounds of formula (I) wherein R1, R2, R3, R25a, R26a, X, and n are as defined in the specification. Pharmaceutical compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and pharmaceutical compositions are also described
Synthesis and evaluation of inhibitors of cytochrome P450 3A (CYP3A) for pharmacokinetic enhancement of drugs
Flentge, Charles A.,Randolph, John T.,Huang, Peggy P.,Klein, Larry L.,Marsh, Kennan C.,Harlan, John E.,Kempf, Dale J.
supporting information; experimental part, p. 5444 - 5448 (2010/05/02)
The HIV protease inhibitor ritonavir (RTV) is also a potent inhibitor of the metabolizing enzyme cytochrome P450 3A (CYP3A) and is clinically useful in HIV therapy in its ability to enhance human plasma levels of other HIV protease inhibitors (PIs). A nov
Asymmetric synthesis of α-alkylated aldehydes using terminal epoxide-derived chiral enamines
Hodgson, David M.,Kaka, Naeem S.
supporting information; experimental part, p. 9958 - 9960 (2009/06/30)
(Chemical Equation Presented) Effective discrimination: Efficient lithium amide-induced terminal epoxide-enamine transformation provides the first enamines capable of generating α-alkylated aldehydes with high asymmetric induction by intermolecular nucleophilic substitution (see scheme).
Lithiation-induced migrations from nitrogen to carbon in terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Xu, Zhaoqing,Ward, John G.
, p. 2245 - 2248 (2008/02/14)
(Chemical Equation Presented) Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valua
Dimerization and isomerization reactions of α-lithiated terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Miles, Steven M.,Brierley, Christopher A. J.,Ward, John G.
, p. 10009 - 10021 (2008/03/28)
(Chemical Equation Presented) The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio-and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy 2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on the nature of the N-protecting group. α-Lithiated terminal aziridines bearing N-alkoxycarbonyl (Boc) protection undergo N- to C-[1,2] migration to give N-H trans-aziridinylesters. In contrast, aziridines bearing N-organosulfonyl [tert-butylsulfonyl (Bus)] protection undergo rapid dimerization to give 2-ene-1,4-diamines or, if a pendant alkene is present, diastereoselective cyclopropanation to give 2-aminobicyclo[3.1.0]hexanes. All of these reactions were used as key steps in the preparation of synthetically and biologically important targets.
Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists
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Page/Page column 26, (2010/11/08)
The present invention provides serotonergic aminoalkylbenzofurans of Formula (I): where R, R1, R2, R3, R4, R4′, R5, R5′, and R12 are as described in the specification.
Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amino ketones
Kawamoto,Wills
, p. 1916 - 1928 (2007/10/03)
Enantioselective transfer hydrogenation of α-amino ketones is an effective method for the asymmetric synthesis of β-hydroxy amines and aziridines.
WITTIG OLEFINATION IN THE ABSENCE OF AN EXOGENOUS BASE: A NEW SYNTHESIS OF α-SUBSTITUTED PRIMARY ALLYLIC AMINES
Dellaria, Joseph F.,Sallin, Kevin J.
, p. 2661 - 2664 (2007/10/02)
A new synthesis of α-substituted primary allylic amines through the in situ generation and trapping of an ylide from the reaction of an N-acyl aziridine, triphenylphosphine, and an aldehyde in refluxing isopropanol is reported.These compounds can be prepared enantioselectively (> 94.6percent ee) by employing a chiral nonracemic N-acyl aziridine.
