83697-66-9Relevant academic research and scientific papers
Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues
Kurouchi, Hiroaki
, p. 653 - 658 (2021/02/06)
A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.
Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
Kurouchi, Hiroaki
, p. 8313 - 8316 (2020/08/17)
Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is
Antagonism of quorum sensing phenotypes by analogs of the marine bacterial secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide
Meschwitz, Susan M.,Teasdale, Margaret E.,Mozzer, Ann,Martin, Nicole,Liu, Jiayuan,Forschner-Dancause, Stephanie,Rowley, David C.
, (2019/07/15)
Quorum sensing (QS) antagonists have been proposed as novel therapeutic agents to combat bacterial infections. We previously reported that the secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide, produced by a marine bacterium identifie
Chemoselective acylation of primary amines and amides with potassium acyltrifluoroborates under acidic conditions
Galvez, Alberto Osuna,Schaack, Cedric P.,Noda, Hidetoshi,Bode, Jeffrey W.
supporting information, p. 1826 - 1829 (2017/02/15)
Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.
Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines
Noda, Hidetoshi,Bode, Jeffrey W.
, p. 4328 - 4332 (2015/01/08)
N-Methyliminodiacetyl (MIDA) acylboronates undergo chemoselective amide-bond forming ligations in water with O-Me hydroxylamines, including unprotected peptide substrates. These bench-stable boronates were easily prepared from potassium acyltrifluoroborat
Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions
Lee, Jeongbin,Muthaiah, Senthilkumar,Hong, Soon Hyeok
, p. 2653 - 2660 (2014/09/17)
An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2]2, with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.
Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water
Dumas, Aaron M.,Molander, Gary A.,Bode, Jeffrey W.
supporting information; experimental part, p. 5683 - 5686 (2012/07/01)
Come together, right now: Acyltrifluoroborates and O-benzoyl hydroxylamines come together to form amides in water (see scheme). The ligations are complete within minutes at room temperature and do not require any reagents or catalysts. The reaction has a broad substrate scope and tolerates unprotected functional groups. Copyright
The mechanism of the α-ketoacid-hydroxylamine amide-forming ligation
Pusterla, Ivano,Bode, Jeffrey W.
, p. 513 - 516 (2012/03/22)
Three-ring circus! Surprisingly complex molecular acrobatics are observed in the mechanism of the α-ketoacid-hydroxylamine amide-forming ligation reaction. Although this remarkable reaction can already be used for the chemoselective union of large, unprotected peptide fragments the elucidated mechanism provides important clues to extending its application to larger and more complex biological targets. Copyright
Structure-activity relationships for a series of bis(phenylalkyl)amines: Potent subtype-selective inhibitors of N-methyl-D-aspartate receptors
Tamiz, Amir P.,Whittemore, Edward R.,Zhou, Zhang-Lin,Huang, Jin-Cheng,Drewe, John A.,Chen, Jie-Cheng,Cai, Sui-Xiong,Weber, Eckard,Woodward, Richard M.,Keana, John F. W.
, p. 3499 - 3506 (2007/10/03)
A series of bis(phenylalkyl)amines, structural analogues of ifenprodil and nylidrin, were synthesized and tested for antagonism of N-methyl-D- aspartate (NMDA) receptors. Potency and subunit selectivity were assayed by electrical recordings in Xenopus ooc
Rapid in-plate generation of benzimidazole libraries and amide formation using EEDQ
Thomas, James B.,Fall, Michael J.,Cooper, Julie B.,Burgess, Jason P.,Carroll, F. Ivy
, p. 5099 - 5102 (2007/10/03)
A solution phase method for the preparation of etonitazene-related benzimidazoles and a general method for the preparation of amide derivatives in 96-well format have been developed for the generation of libraries of compounds in parallel.
