Aminoalkylation of Electron-Rich Aromatic Compounds Using Performed Iminium Salts Derived from Aldehydes other than Formaldehyde

Syntheses and Transformations of 1-(α-Aminobenzyl)-2-Naphthol Derivatives

“…This strategy was first applied by Risch et al 26 to prepare 12 and 14 (Scheme 5), and was extended by Saidi et al 27 the iminium salts being prepared in situ in 5 M ethereal lithium perchlorate to obtain 13 and 15 (Scheme 5). and its absolute configuration was found to be (S) (determined by X-ray diffraction analysis of its hydrobromide salt, 3a.HBr).…”

Convenient and Efficient Method for the Synthesis of N‐Heteroaryl Aminonaphthols under Solvent‐Free Conditions

“…Katritzky et al 3 have reported an improved aminoalkylation of 2-naphthol and phenol derivatives with prefor med iminium salts derived from aromatic aldehydes, in a two-step sequence with 26%-92% yields. Moreover, aminoalkylation of electron rich aromatic compounds such as 2-naphthol for the synthesis of Betti base derivatives [4][5][6][7][8][9][10][11][12][13][14] in the presence of LiClO 4 , Sc(OTf) 3 , Yb(OTf) 3 , La(OTf) 3 , YbCl 3 , TiCl 4 and Me 3 SiCl as catalysts has been reported. [15][16][17] The racemic aminonaphthols (Betti bases) have been used for transformation into products with anti bacterial activity.…”

An Efficient Synthesis of Novel α‐Aminophosphonates Based on a Mannich‐Type Reaction

“…[10] In the course of our studies on modern variants of the Mannich reaction we have disclosed highly diastereoselective methods for the aminoalkylation of activated carbonyl compounds, for example, enamines or imines, with various ternary iminium salts. [11] This strategy has been applied successfully to the direct aminoalkylation of ketones, [12] α-branched aldehydes, [13] electron-rich aromatic compounds [14] and vinylogous nucleophiles. [15] Some examples of Mannich-type reactions involving phosphanes, phosphinates, phosphorus acids and phosphonates have previously been reported in the literature, but the reaction products are relatively simple and the reaction procedure cannot be employed with a variety of aldehydes and amines.…”