66614-71-9Relevant academic research and scientific papers
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics
Morofuji, Tatsuya,Shimizu, Akihiro,Yoshida, Jun-Ichi
supporting information, p. 9816 - 9819 (2015/08/24)
A new approach for electrooxidative coupling of aromatic compounds and primary alkylamines bearing a functional group such as a hydroxyl group and an amino group was developed. The key to the success of the transformation is heterocyclization of functional primary alkylamines. Treatment of primary alkylamines bearing a functional group with nitriles or their equivalents gives the corresponding heterocycles. The electrochemical oxidation of aromatic substrates in the presence of the heterocycles followed by chemical reaction under nonoxidative conditions gave the desired coupling products.
Intramolecular nucleophilic deselenenylation reactions promoted by benzeneselenenyl triflate. Stereospecific synthesis of vicinal amino alcohol precursors
Tingoli, Marco,Testaferri, Lorenzo,Temperini, Andrea,Tiecco, Marcello
, p. 7085 - 7091 (2007/10/03)
After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides, containing internal oxygen or nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and oxazolidin-2-ones has been developed.
A New and General Route to N-Protonated Azomethine Ylides from N-(Silylmethyl)amidines and -thioamides. Cycloaddition of Synthetic Equivalents of Nitrile Ylides
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 1997 - 2004 (2007/10/02)
The N- or S-alkylation or -silylation of N-(silylmethyl)amidines or -thioamides and the subsequent desilylation of the silylmethyl group generate N-protonated azomethine ylides bearing a leaving group.These azomethine ylides undergo successful cycloaddition with electron-deficient olefins, acetylenes, and aldehydes.As the leaving group is eliminated under the reaction conditions, these azomethine ylides can be synthetic equivalents of nonstabilized nitrile ylides which are otherwise relatively inaccessible.
N-PROTONATED AZOMETHINE YLIDES WITH A LEAVING GROUP AS SYNTHETIC EQUIVALENTS FOR NONSTABILIZED NITRILE YLIDES
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 1411 - 1414 (2007/10/02)
Through alkylation or silylation and then desilylation steps, N-(silylmethyl)amidines generate N-protonated azomethine ylides which cycloadd to olefins, acetylenes, and aldehydes giving 1- or 2-pyrrolines, pyrroles, and 2-oxazolines, respectively, after the elimination of N-substituted anilines.With this sequence, the amidines are useful synthetic equivalents of nonstabilized nitrile ylides.
Reactions of 1,2- and 1,3-amino-alcohols with imidate salts and with ortho esters
Butt, Mohammed I.,Neilson, Douglas G.,Watson, Kathleen M.,Zakir-Ullah
, p. 2328 - 2332 (2007/10/04)
ω-Hydroxy-N-substituted amidines have been shown to be the intermediates in the formation of 2-oxazolines and 5,6-dihydro-4H-1,3-oxazines from the reactions of imidates and 1,2- and 1,3-amino-alcohols respectively, 1,2- and 1,3-Amino-alcohols also react with ortho esters to give 2-oxazolines and 5,6-dihydro-4H-1,3-oxazines, but N-acylamino-alcohols give rise to oxazolidines with ortho esters.
