35948-04-0Relevant academic research and scientific papers
C-H Insertion by Alkylidene Carbenes to Form 1,2,3-Triazines and Anionic [3 + 2] Dipolar Cycloadditions to Form Tetrazoles: Crucial Roles of Stereoelectronic and Steric Effects
Chen, Fa-Jie,Lin, Yongjia,Xu, Man,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
supporting information, p. 718 - 723 (2020/01/31)
The synthesis of 1,2,3-triazines and bicyclic tetrazoles from α-azido ketones is described. The common intermediate generated from lithiated trimethylsilyldiazomethane and α-azido ketones diverges depending on the steric bulk of the substituents. The form
Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 6549 - 6552 (2016/06/01)
The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.
Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists
Perner, Richard J.,Koenig, John R.,Didomenico, Stanley,Gomtsyan, Arthur,Schmidt, Robert G.,Lee, Chih-Hung,Hsu, Margaret C.,McDonald, Heath A.,Gauvin, Donna M.,Joshi, Shailen,Turner, Teresa M.,Reilly, Regina M.,Kym, Philip R.,Kort, Michael E.
supporting information; experimental part, p. 4821 - 4829 (2010/08/06)
The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the t
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
Dynamic kinetic resolution of β-azido alcohols. An efficient route to chiral aziridines and β-amino alcohols
Pamies,Baeckvall
, p. 4022 - 4025 (2007/10/03)
Enzymatic resolution of β-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic β-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis of (S)-propanolol I and (R)-β-azido-α-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.
The reactivity of polyfunctionalized iminophosphoranes
Carite,Alazard,Ogino,Thal
, p. 7011 - 7014 (2007/10/02)
The reactivity of some functionalized azides has been studied under the conditions of the Staudinger and aza-Wittig reactions. With the azides having a trifluoroacetamido group in the ortho-position of the aromatic ring, intramolecular reactions have been observed which allow new synthetic approaches to indoline and imidazoindole compounds.
