Tertiary amine moiety

Local anesthetics are positively charged amphiphiles in solution. We have selected hydrochlorides of dibucaine (DBC H ), procaine (PRC H ), tetracaine (TTC H ), and lido-caine (LDC H ). All of these drugs are structurally similar they consist of the substituted benzene ring and tertiary amine moieties, as shown by (VI)-(IX) in Fig. 1. The presence of the positive charge increases the solubility in water and in consequence, the anesthetic efficiency. 

Photoinduced intramolecular interaction of t-S and tertiary amine moieties linked with a polymethylene chain has also been studied24. The photoexcitation of fraws-stilbene in which a tertiary amine is attached to the ortho position with a (CH2)i-3 linker leads to fluorescent exciplexes by intramolecular electron transfer, and results in no more than trans-cis isomerization. The failure to give adducts from the intramolecular exciplexes could arise from the unfavourable exciplex geometry to undergo the necessary bond formation. 

The scope of Michael additions with catalysts containing cyclohexane-diamine scaffolds was broadened by Li and co-workers [95]. When screening for a catalyst for the addition of phenylthiol to a,p-nnsatnrated imides, the anthors fonnd that thiourea catalyst 170 provided optimal enantioselectivities when compared to Cinchon alkaloids derivatives (Scheme 41). Electrophile scope inclnded both cyclic and acyclic substrates. Li attributed the enantioselectivity to activation of the diketone electrophiles via hydrogen-bonding to the thiourea, with simultaneous deprotonation of the thiol by the tertiary amine moiety of the diamine (170a and 170b). Based on the observed selectivity, the anthors hypothesized that the snbstrate-catalyst... 

Kudoh R, Sudo A, Endo T (2009) Synthesis of eight-membered lactone having tertiary amine moiety by ring-expansion reaction of 1,3-benzoxazine and its anionic ring-opening polymerization behavior. Macromolecules 42 2327-2329... 

Table 10. Photoinduced homopolymerization and graft-copolymerization of EHMA in the presence of equimolar combinations of tow- and high-molecular-weight systems based on benzophenone/tertiary amine moieties [52]...

Table H. UV curing in film matrix of HDDA/APDG and HDDA/BA equimolar mixtures, under nitrogen, by photoinitiatois based on both benzophenone and tertiary amine moieties [18,22, 53]...

One way of minimizing the detrimental effect caused by chain transfer on decreasing molecular weight and crosslink density of UV curable coatings has been successfully applied [115] by using copolymerizable methacrylic monomers containing the tertiary amine moiety as components of reactive acrylic formulations in the presence of benzoin ether derivatives. 

In this context, polymeric photoinitiators bearing side-chain benzoin methyl ether and tertiary amine moieties in the same macromolecule, have been prepared and the effect of amine on the photoinitiation activity investigated [116-118]. 

The large-scale pilot plant preparation of the chiral aminochroman antidepressant ebaizotan (also known as NAE-086) was developed by H.J. Federsel and co-workers. The structural features of the target included a disubstituted chroman skeleton, a stereocenter, as well as a non-symmetrical tertiary amine moiety at the C3 position and a secondary carboxamide group at C5. The backbone of the target molecule was constructed using the Perkin condensation of 2-hydroxy-6-methoxybenzaldehyde with hippuric acid under mild conditions. 

Intermolecular trapping of the iminium cation, generated by the sensitized PET reaction of tertiary amine moiety using A,AT -dimethyl-2,7-diazapyrelium-bis tetrafluoroborate salt as an electron acceptor, by MejSiCN is reported by... 

Baars et al. reported the peripheral amine modification of PPI frameworks with adamantane isocyanate to afforded terminal urea moieties. Supramolecular surface ordering of carboxylic acid-modified urea guests was achieved based on ionic-acid-base association at the outermost dendritic tertiary amine moieties and urea promoted H-bonding. Tj relaxations were found to significantly increase at the complex surface verifying enhanced rigidity. Other assemblies of interest include PAMAM-fatty acid and PAMAM-surfactanf" mixtures. 

Triglycidyl Ether of p-Aminophenol. The triglycidyl derivative of p-aminophenol was originally developed by Union Carbide (58) and is currently marketed by Huntsman under the designation MY 0500 and 0510. Epoxidation of p-aminophenol is carried out with a large excess of epichlorohydrin under carefiilly controlled conditions, since the triglycidylated resin exhibits limited thermal stability and polymerizes vigorously under the influence of its tertiary amine moiety. 

Quatemization (the reaction between alkyl bromide and tertiary amine moiety) has been reported for the attachment of Choi moieties onto a (co)polymer backbone... 

The dual activation mode of the aforementioned cinchona alkaloid-derived thiourea catalysts proved to be highly effective in catalyzing the asynunetric Mannich reaction, among other transformations. These findings prompted the development of new, more simple bifunctional chiral catalysts that are predominately based on tra 5 -l,2-diaminocy-clohexane. For example, the application of the thiourea catalyst 120, which was developed by Takemoto and coworkers, afforded upon the reaction of Af-Boc-protected imines with diethyl malonate the desired chiral amines in good chemical yields (up to 91%) and enantioselectivities (98% ee) (Scheme 11.23) [81]. The catalytic mechanism presumably involves deprotonation and coordination of the active carbonyl compound by the chiral tertiary amine moiety. The formed enolate then attacks the si-face of the... 

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