Montmorillonite K-10 catalyzed Mannich reaction: Synthesis of aminonaphthoquinone derivatives from Lawsone

Abstract

An efficient one-pot protocol for the synthesis of 2-((substituted amino)(4-phenyl)methyl)-3-hydroxy-naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and anilines/heterocyclic amines using montmorillonite K-10 as a catalyst. The advantages of this method include short reaction time, excellent yield and easy work-up.

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

“… 257 In addition, S. Jayashree and K. Shivashankar also performed the same reaction in the presence of montmorillonite K-10 using ethanol as the solvent at room temperature. 258 The reaction conditions, time and range of yields of these methods are summarized in Scheme 141 .…”

Mannich bases derived from lawsone and their metal complexes: synthetic strategies and biological properties

“…Montmorillonite K-10 is likely to enhance the rate of Mannich reaction. 58 Lopez-Lopez et al developed a non-catalytic effective procedure to prepare Mannich base lawsone derivatives 54 in 80-94% yields using one-pot three-component reaction of lawsone (2), amines and benzaldehyde promoted by ultrasound irradiation at room temperature for 15 min (Scheme 32). 59 A possible mechanism for the formation of 54 is proposed according to the rst mechanism as indicated in Scheme 2.…”

One-pot synthesis of indole-fused nitrogen heterocycles via the direct C(sp2)–H functionalization of naphthoquinones; accessibility for deep red emitting materials

“…Generally, mono-substituted (naphtho)quinone derivatives are primarily utilized as substrates to obtain their vicinal disubstituted products. [16][17][18][19][20][21][22][23] Only a limited number of reports are available on the transformation of unmodified naphthoquinone to the corresponding vicinal disubstituted derivatives through direct C(sp 2 )-H functionalization. Wang and co-workers reported the one-pot vicinal amine-alkylation of naphthoquinone in the presence of copper(II) triflate and di-tbutyl peroxide (Chart 1).…”