Simple and Efficient Synthesis of Novel bis-Betti Bases via a One-Pot Pseudo-Five-Component Reaction

Recent advances in the synthesis and synthetic applications of Betti base (aminoalkylnaphthol) and bis-Betti base derivatives

“…This reaction worked well with heteroaromatic amines such as 2-aminopyrimidines and 2-aminopyridine derivatives and afforded desired products in 81-91% yields (Scheme 115). 123 Abdul and Hussain 124 have exploited an efficient method for the synthesis of N,N 0 -bis-[(2-hydroxynapthalene-1-yl)(substituted phenyl)methyl]-2,6-diaminopyridine derivatives 165 by one-pot three-component reaction of 2-naphthol, 2,6-diaminopyridine and substituted aromatic aldehydes in ethanol at 80 C within 24-120 h and under microwave irradiation within 2-6 min at high power (400-900 W) without any catalyst. The isolated yields in ethanol condition (up to 98%) are higher than in microwaveassisted solvent-free condition (up to 42%) (Scheme 116).…”

Recent Developments on Five-Component Reactions

“…6C5CR for bis(1-aminomethyl-2-hydroxy)naphthalenes. The Olyaei group reported a solvent-free 6C5CR for the synthesis of bisBetti bases (bis(1-aminomethyl-2-hydroxy)naphthalenes) 88 using two equiv each of aryl aldehydes and heteroaryl amines and one equiv of 2,3-dihydroxynaphthalene under the catalysis of formic acid at 80 • C (Scheme 37) [51].…”

A Green Protocol for One‐Pot Pseudo Five‐Component Synthesis of a New Series of Bis‐Betti Bases Via Mannich‐Type Reaction

“…The synthetic routes for the synthesis of this scaffold have been reviewed. [5][6][7][8] Moreover, bis-aminomethylnaphthols (bis-Betti bases) have been synthesized using by the reaction of various types of dihydroxynaphthalens such as 2,6-dihydroxynaphthalene and 2,3-dihydroxynaphthalene with aldehydes and amines, [9][10][11][12][13] the reaction of diamines such as 2,6-diaminopyridine, piperazine and p-phenylenediamine with naphthols and aldehydes, [14][15] and the reaction of dialdehydes such as terephthaldehyde and isophthalaldehyde with naphthols and amines [16][17] and reduction of bisdihydrooxazine structures. [18] The Betti reaction produces racemic and nonracemic aminoalkylnaphthol ligands.…”