Journal ArticleDOI
Cesium effect: high chemoselectivity in direct N-alkylation of amines
TLDR
The results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation, offering wide applications in peptidomimetic syntheses.Abstract:
A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.read more
Citations
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Journal ArticleDOI
Regioselective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones: Screening of their biological activities against Ca2+-ATPase
Salil Putatunda,Srabasti Chakraborty,Swatilekha Ghosh,Pinki Nandi,Supriya Chakraborty,Parimal C. Sen,Arijit Chakraborty +6 more
TL;DR: In inhibitory action of both the 3,4-dihydropyrimidin-2(1H)-ones and the N1-alkylated derivatives were tested on Ca( 2+)-ATPase, which revealed that the parent compounds can act as Ca(2+)- ATPase inhibitors whereas the N 1-alkYLated derivatives are inefficient for this purpose.
Journal ArticleDOI
Synthesis and Conformational Analysis of Locked Carbocyclic Analogues of 1,3-Diazepinone Riboside, a High-Affinity Cytidine Deaminase Inhibitor
Olaf R. Ludek,Gottfried K. Schroeder,Chenzhong Liao,Pamela Russ,Richard Wolfenden,Victor E. Marquez +5 more
TL;DR: The results demonstrate CDA’s binding preference for a south sugar pucker in agreement with the high-resolution crystal structures of other CDA inhibitors bound at the active site.
Journal ArticleDOI
Copper catalysed synthesis of indolylquinazolinone alkaloid bouchardatine
Mayavan Viji,Rajagopal Nagarajan +1 more
TL;DR: In this paper, the total synthesis of indolylquinazolinone alkaloid bouchardatine and some of its quinazolone derivatives is described.
Journal ArticleDOI
Dialkyl phosphite as a highly selective mono-N-alkylating agent using indium triflate under microwave irradiation
TL;DR: Indium triflate catalyzed selective mono-N-alkylation of primary amines using dialkyl phosphite as an alkylating agent under microwave irradiation was reported in this article.
Journal ArticleDOI
Computational study of carbon–hydrogen bond deprotonation by alkali metal superbases
TL;DR: In this article, the role of alkali metal amide superbases in the degradation of hydrocarbon C-H bonds is analyzed with the use of density functional theory calculations.
References
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Book
Reagents for Organic Synthesis
TL;DR: In this paper, the authors propose a method for using Reference Abbreviations (RABs) as a reference abbreviation for reference abbreviations in the context of bioinformatics.
Journal ArticleDOI
Synthesis of secondary amines
Journal ArticleDOI
An assessment of the causes of the cesium effect
TL;DR: In this paper, the effect of this effect on macrocyclization by means of nucleophilic substitution is discussed. But it is concluded that the cesium ion is virtually completely solvated and that carboxylates are essentially free and highly reactive.