858259-47-9Relevant articles and documents
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Loudon,Shulman
, p. 1618,1621 (1938)
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Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids
Gazitúa, Marcela,Tapia, Ricardo A.,Contreras, Renato,Campodónico, Paola R.
supporting information, p. 2611 - 2618 (2014/06/09)
Solvation effects on the reaction mechanism of the title reactions have been kinetically evaluated in 21 conventional solvents and 17 ionic liquids. Solvent polarity affects the catalyzed and non-catalyzed SNAr pathways differently. The ambiphi
One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides
Crich, David,Sasaki, Kaname,Rahaman, Md Yeajur,Bowers, Albert A.
supporting information; experimental part, p. 3886 - 3893 (2009/10/20)
(Chemical Equation Presented) Opening cyclic monothioanhydrides by amines provides a convenient entry into amido thioacids that can be trapped in situ by 2,4-dinitrobenzenesulfonamides, by electron-deficient azides, or by amines in the presence of Sanger's reagent leading, in each case, to dissymmetric diamides in what can be considered a one-pot, three-component coupling sequence. The use of monothiomaleic anhydride and bifunctional nucleophiles such as amino thiols provides access to heterocyclic amides. The low reactivity of cyclic monothioanhydrides toward alcohols enables the use of methanol as solvent and obviates the need for the protection of alcohols in the various reaction components. Reaction of N-benzyloxycarbonyl-L-aspartic monothioanhydride with unprotected glycosyl amines, followed by capture of the thioacid intermediate with N-sulfonyl amino acid derivatives results in a three-component convergent synthesis of glycosylated peptides.
