By Julio Alvarez-Builla, Juan Jose Vaquero, José Barluenga
The must-have reference within the box of heterocyclic compounds, comprehensively protecting their synthesis, constitution and chemical and actual properties.By providing basically the $64000 evidence, this instruction manual succeeds in being whole whereas containing the knowledge in exactly volumes.An updated resource of high quality info for all natural and medicinal chemists operating during this box in and academia.
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85) are conveniently prepared from methyl acrylate (83) or its derivatives by the copper-catalyzed addition of N,N-dichlorotosyl sulfonamide and subsequent ring closure . Alternatively, these products can be accessed by treating a,b-dibromoesters with simple primary amines . 4 Ring Contraction of Other Heterocycles Aziridines can be accessed through the extrusion of elements from larger nitrogenous heterocycles, most notably triazolines. 19). Photolysis of these compounds in a quartz reaction vessel using a mediumpressure mercury lamp led to efﬁcient formation of the fused tricyclic aziridine 88 .
In this case, the solvent itself is presumed to fulﬁll the role of Lewis acid . An operationally attractive procedure has been reported in which the aldimine is formed in situ using lithium perchlorate as a catalyst (entry 3), providing exclusively the cis isomer . Acive methylene compounds serve as useful carbenoid precursors (in the form of phenyliodonium ylides) by treatment with iodobenzene diacetate and a catalytic amount of base under very mild conditions. Thus, tosylaldimines are converted into the corresponding aziridines in a one-pot procedure without the need for a metal catalyst .
109 j 2 Three-Membered Heterocycles. Structure and Reactivity 32 can exhibit impressive enantioselectivity under the inﬂuence of the Schiff base/ amino acid copper(II) complex dimer 100, although relatively high catalyst loadings must be used . Acetylide anions are also competent nucleophiles when a copper(I) catalyst is used, as demonstrated by the high-yielding conversion of the 2-alkylaziridine 102 into the homopropargylamine 104, resulting from attack at the less hindered carbon .