4393-14-0Relevant academic research and scientific papers
One-pot Synthesis of a 1,3,7,9-Tetraazacyclododecane Derivative and an Investigation of its Complexation Properties
Axen, Andreas,Grennberg, Helena,Gogoll, Adolf
, p. 712 - 713 (1998)
A one-pot synthesis of a 1,3,7,9-tetraazacyclododecane macrocycle in 37% yield from inexpensive starting materials is described, and its complexation properties with metal cations are investigated.
Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group
Shao, Yinlin,Zhang, Fangjun,Zhang, Jie,Zhou, Xigeng
supporting information, p. 11485 - 11489 (2016/10/24)
Lanthanide-catalyzed alkynyl exchange through C?C single-bond cleavage assisted by a secondary amino group is reported. A lanthanide amido complex is proposed as a key intermediate, which undergoes unprecedented reversible β-alkynyl elimination followed by alkynyl exchange and imine reinsertion. The in situ homo- and cross-dimerization of the liberated alkyne can serve as an additional driving force to shift the metathesis equilibrium to completion. This reaction is formally complementary to conventional alkyne metathesis and allows the selective transformation of internal propargylamines into those bearing different substituents on the alkyne terminus in moderate to excellent yields under operationally simple reaction conditions.
Development of a Large-Scale Route to an MCH1 Receptor Antagonist: Investigation of a Staudinger Ketene-Imine Cycloaddition in Batch and Flow Mode
Karlsson, Staffan,Bergman, Rolf,L?fberg, Christian,Moore, Peter R.,Pontén, Fritiof,Tholander, Joakim,S?rensen, Henrik
, p. 2067 - 2074 (2016/01/08)
A practical large-scale route to an MCH1 receptor antagonist is described. A Staudinger β-lactam synthesis of an imine and an in situ generated ketene was utilized as a key step for the preparation of a spiro-azetidine building block. The reaction was demonstrated in both batch and flow mode and a comparison of these techniques is described.
Synthesis of imines from amines in aliphatic alcohols on Pd/ZrO2 catalyst under ambient conditions
Cui, Wenjing,Zhaorigetu, Bao,Jia, Meilin,Ao, Wulan,Zhu, Huaiyong
, p. 2601 - 2604 (2014/01/06)
Synthesis of imines from amines and aliphatic alcohols (C 1-C6) in the presence of base on supported palladium nanoparticles has been achieved for the first time. The catalytic system shows high activity and selectivity in open air at room temperature.
Method of synthesis of phosphinic acids based on hypophosphites: VIII.1 synthesis of α-aminoalkylphenethylphosphinic acids
Dmitriev,Ragulin
experimental part, p. 1786 - 1791 (2012/01/12)
Development of methodology of double Arbuzov rearrangement based on hypophosphites allows a one-pot formation of two unsymmetrical phosphorus-carbon bonds by the Michael-Pudovik type reaction of stepwise addition of the intermediately forming silyl esters of trivalent phosphorus to different unsaturated compounds. A procedure was developed of the synthesis of α-aminoalkylphenethylphosphinic acids. Bis-(trimethylsilyl) phenethylphosphonite formed as a result of the addition of bis(trimethylsilyl) hypophosphite to styrene in situ was added without isolation from the reaction mixture to Schiff bases obtained preliminary from benzylamine or diphenylmethylamine and various aldehydes. The subsequent removal of N-protecting groups by hydrogenation or acidic hydrolysis gave a number of new α-aminoalkylphenethylphosphinic acids.
Seven-component reactions by sequential chemoselective Ugi-Mumm/Ugi-Smiles reactions
Brauch, Sebastian,Gabriel, Lars,Westermann, Bernhard
supporting information; experimental part, p. 3387 - 3389 (2010/07/06)
A seven-component reaction was accomplished by utilizing the different chemoselectivities of the Ugi-Mumm and the Ugi-Smiles reaction. The sequential multicomponent reactions led to highly diverse peptide and glycopeptide like structures.
Generation and application of o-Quinone methides bearing various substituents on the benzene ring
Sugimoto, Hiromichi,Nakamura, Satoshi,Ohwada, Tomohiko
, p. 669 - 679 (2008/02/09)
o-Quinone methides (o-QMs) are highly reactive, short-lived intermediates, which have potential synthetic applicability. However, few studies on the generation of o-QMs bearing an electron-withdrawing group have been reported. Herein we present a general method for the generation of o-QMs, particularly those substituted with an 0lectrophilic substituent, from new precursors, 4H-1,2-benzoxazines 2. We have also studied systematically the Diels-Alder reactions of o-QMs with various dienophiles, such as vinyl ethers, enamines and imines. The reactions provide a versatile route to substituted chromans, phenols and 3,4-dihydro-2H-benzo[e]-[1,3]oxazines (3,4-dihydro-1,3-benzoxazines). Furthermore, we applied the new method to the derivatization of some natural products.
A stable, convertible isonitrile as a formic acid carbanion [ -COOH] equivalent and its application in multicomponent reactions
Kreye, Oliver,Westermann, Bernhard,Wessjohann, Ludger A.
, p. 3188 - 3192 (2008/09/20)
The application of 2-(2,2-dimethoxyethyl) phenyl isonitrile in Ugi, Passerini, and Ugi-Smiles reactions is described. The simple transformation to highly activated indolyl amides allows functional-group conversion of the isonitrile moiety into a variety of carboxylic acid derivatives, overall acting as a neutral, nucleophilic COOH equivalent. Georg Thieme Verlag Stuttgart.
An enantioselective chiral Bronsted acid catalyzed imino-azaenamine reaction
Rueping, Magnus,Sugiono, Erli,Theissmann, Thomas,Kuenkel, Alexander,Kockritz, Angela,Pews-Davtyan, Anahit,Nemati, Navid,Beller, Matthias
, p. 1065 - 1068 (2007/10/03)
(Chemical Equation Presented) The enantioselective Bronsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3′-di(phenanthryl)-H8-BINOL. The corresponding ami
