120803-35-2Relevant academic research and scientific papers
Classical benzotriazole-mediated α-aminoalkylations of alkynes: Synthesis and characterization of alk-2-yn-1-amines as amphiphilic materials
Idzik, Krzysztof R.,Cabaj, Joanna,Soloducho, Jadwiga,Abdel-Fattah, Ashraf A. A.
, p. 1672 - 1680 (2007)
Reactions of readily available and stable benzotriazolemethanamines 1a-1, obtained from aldehydes and secondary amines (Scheme 2), gave the expected alk-2-yn-1-amines 3a-t (Scheme 3). The amphiphilic character of the synthesized products was responsible f
Chemo- and diastereoselective cyclopropanation of allylic amines and carbamates
Csatayová, Kristína,Davies, Stephen G.,Lee, James A.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
experimental part, p. 8420 - 8440 (2010/12/20)
A highly chemo- and diastereoselective protocol for the cyclopropanation of tertiary allylic amines with Shi's carbenoid [CF3CO 2ZnCH2I] is described. The high levels of diastereoselectivity observed in these reactions may be attributed to chelation of the nitrogen atom to the zinc reagent, which then transfers a methylene unit to the syn-face of the olefin. Furthermore, a stereodivergent protocol for the cyclopropanation of a range of allylic carbamates has been developed, which provides access to both diastereoisomers of the corresponding cyclopropanes with very high levels of diastereoselectivity: cyclopropanation with the Wittig-Furukawa reagent [Zn(CH2I)2] proceeds under chelation control to give the corresponding syn-product, whilst reaction with Shi's carbenoid proceeds under steric control to give the corresponding anti-cyclopropane, in >95:5 dr in both cases.
Aminoalkylations of esters, sulfones, sulfoxides, alkylated pyridines, and nitriles with in situ generated iminium ions
Katritzky, Alan R.,Idzik, Krzysztof R.,Abdel-Fattah, Ashraf A. A.,Soloducho, Jadwiga,Steel, Peter J.
, p. 3377 - 3388 (2008/02/10)
N-(α-Aminoalkyl)benzotriazoles, prepared from a variety of aldehydes and secondary amines, react with diverse ester enolates, sulfones, a sulfoxide, alkylated pyridines, and nitriles to provide novel access to β-amino carboxylic esters (55-80% yield), β-aminoalkyl sulfones (42-88% yield), β-aminoalkyl sulfoxides (20-32% yield), α- and γ-(β- aminoalkyl)pyridines (69-90% yield), and β-aminoalkyl cyanides (10-97% yield), respectively. Georg Thieme Verlag Stuttgart.
Synthesis of vinylogous β-amino esters from N-(N,N-dialkylaminoalkyl)benzotriazoles
Aurrecoechea, Jose M.,Fernandez, Alvaro,Gorgojo, Jose M.,Suero, Ruben
, p. 693 - 702 (2007/10/03)
Treatment of N-(N,N-dialkylaminoalkyl)benzotriazoles with 4- bromocrotonates in the presence of zinc provides a new route to 5-(N,N-dialkylamino)-2-alkenoate esters. This is formally the result of the γ-addition of zinc dienolate reagents to iminium catio
EPR studies on the Sml2-promoted coupling of N-(N′,N′-dialkylaminoalkyl)benzotriazoles
Katritzky, Alan R.,He, Hai-Ying,Qiu, Guofang,Bratt, Peter J.,Parrish Jr., Sidney H.,Angerhofer, Alexander
, p. 1755 - 1757 (2008/02/11)
(formula presented) Radicals generated in the Sml2-promoted coupling of N-(N′,N′-dialkylaminoalkyl)benzotriazoles 1 have been detected using the EPR spintrapping technique. Single electron transfer (SET) between 1 and Sml2 is discuss
Synthesis of N-[1-(trialkylstannyl)alkyl]amides and -amines by the displacement of benzotriazoles with trialkylstannyllithiums
Pearson,Stevens
, p. 904 - 906 (2007/10/02)
Condensation of benzotriazole, an aldehyde, and either an amine or amide using the method of Katritzky gave N-[1-benzotriazol-1-yl)alkyl]amides and -amines, which were treated with tributylstannyllithium or trimethylstannyllithium to afford N-[1-(trialkylstannyl)alkyl]amides and -amines, respectively. These compounds are important precursors of nitrogen-substituted organolithium reagents.
The Chemistry of N-Substituted Benzotriazoles. Part 14. Novel Routes to Secondary and Tertiary Amines and to N,N-Disubstituted Hydroxylamines
Katritzky, Alan R.,Yannakopoulou, Konstantina,Lue, Ping,Rasala, Danuta,Urogdi, Laszlo
, p. 225 - 233 (2007/10/02)
Tertiary amines of types R4R3CHNR1R2 (2), (R2CH2)2NR1 (10) and 11, or (R2CH2)3N (12), secondary amines of type (R2CH2)2NH (8), and N,N-disubstituted hydroxylamines of type (R2CH2)2NOH (9), are prepared in high yield by the action of Grignard reagents or sodium borohydride on easily available N,N-dialkyl-N-amines (1) or tris(benzotriazolylmethyl)amine (7), on bis(benzotriazolylmethyl)amines (3), (5), and (6), and on N,N-bis(benzotriazolylmethyl)hydroxylamine (4), respectively.
THE CHEMISTRY OF N-SUBSTITUTED BENZOTRIAZOLES. PART 18. A STUDY OF THE INFLUENCE OF STRUCTURE ON THE 1- TO 2-(N,N-DIALKYLAMINOALKYL)BENZOTRIAZOLE EQUILIBRIUM
Katritzky, Alan R.,Yannakopoulou, Konstantina
, p. 1121 - 1134 (2007/10/02)
The equilibrium constants, the associated free energies for the equilibria, and the free energies of activation for the isomerization process of a series of 1- and 2-(N,N-dialkylaminoalkyl)benzotriazoles of types (8)-(11) were calculated from the variable temperature 1H-nmr spectra.Trends in the magnitudes of these energies and equilibrium constants are correlated with the molecular structure.
A New General Method for the Synthesis of Tertiary Propargylamines (N,N-Dialkyl-2-alkynamines)
Katritzky, Alan R.,Gallos, John K.,Yannakopoulou, Konstantina
, p. 31 - 33 (2007/10/02)
A new method has been developed for the preparation of propargylamines, compounds of pharmaceutical interest.The method employs mild conditions, affords good overall yields, and is succesfully applied even in cases where other methods fail.
