The Synthesis and Conformational Behavior of N, N′,N″‐Trimethyltrianthranilide

Abstract

=9.3f0.2 kcal mol-') than for (5) (AG&,.=17.1 kcal mol-'). We believe there are two principal reasons for this difference: (i) the absence of methyl substituents in the ortho positions of the aromatic rings, and (ii) conjugative stabilization between the lone pairs on sulfur and the K system of the benzene rings in the inversion transition state.

Synthesis and complexing properties of cyclic benzylopeptoids – a new family of extended macrocyclic peptoids

“…The synthesis started with a carboxyl group methylation of the commercially available para-(bromomethyl)phenylacetic acid (9) to provide the corresponding methyl acetate (10). 44 The meta-isomer was elaborated in two steps: first, methylation of the inexpensive meta-tolylacetic acid (11), and then an NBS-mediated benzylic bromination (in nontoxic ethyl acetate). Both of the fairly stable brominated intermediates (10 and 13) were subjected to an amination reaction in the presence of five equivalents of methoxyethylamine (in order to prevent polyalkylation adducts) and the products were isolated after column chromatography as the free amines (the eluent contained 1% triethylamine).…”

“…Benzanilides, [11][12][13] paracyclophanamides, [14][15][16] and arylopeptoids [17][18][19][20][21][22][23][24][25] (Fig. 1) are examples of new types of compounds with promising potential due to their rigidified frame.…”

“…Thus, with the aim of unveiling the full potential of the newly conceived "extended peptoids" [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] within the field of supramolecular chemistry, herein we report theoretical studies, efficient monomer syntheses, solid-phase oligomerization and cyclization of six members of a new class of cyclic oligomeric N-methoxyethyl(aminomethyl) phenylacetamides: the cyclic benzylopeptoid trimers 3-5 and tetramers 6-8 (Fig. 4).…”