New synthetic routes to macrocyclic triamines

Abstract

1,5,9-Triazacyclododecane and related macrocyclic triamines can be conveniently constructed around a single carbon atom as template; this route permits the preparation of selectively alkylated derivatives.

[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

“…Boc-protected N-(3-azidopropyl) [12]aneN 3 (5) was obtained from the azide substitution reaction with Boc-protected N-(3-bromopropyl) [12]aneN 3 (4), which was prepared through the reaction of [12]aneN 3 precursor [30] (2) with 1,3-dibromopropane and further hydrolysis (3) and protection by (Boc) 2 O. Another starting material, 1,5-bis(acetynyl) BODIPY 6, was obtained according to literature method [31].…”

Carboxy Ester Hydrolysis Promoted by Two New Bimetallic Macrocyclic Complexes. Synthesis, Characterization and Catalytic Activity

“…Solvents were dried by conventional procedures and all samples were thoroughly dried prior to elemental analyses. Orthodiaminde (III) (see Scheme 1) was prepared according to previous literature [11]. The C, H and N elemental analyses were performed on a Vario EL-III instrument.…”

“…In the early stage of this work, the key orthoaminde (I) was prepared as previously reported [16,17], using the [12]aneN 3 synthesized by a modified literature procedure [18], although lengthier, than from the commercially available source. The alternative route, proposed later by Weisman [11], provided a very efficient twostep synthesis of (III), via a guanidinium salt obtained from inexpensive starting materials, as opposed [12]aneN 3 itself.…”

Monofunctionalization of Symmetric Difunctional Substrates

“…The selectivity of acylations or alkylations of polyamines can also be modulated by protonation [78] or by conversion to cyclic aminals [71,79,80]. The latter strategy has, for instance, been used successfully for the preparation of monofunctionalized 1,4,7-triazacyclononanes (Scheme 10.18).…”