One-Pot Solvent- and Catalyst-Free Synthesis of Some New Heteroarylaminonaphthoquinones from Lawsone

Abstract

: A clean and efficient one-pot protocol for the synthesis of a series of new 2-hydroxy-3-((3-aryl)(heteroarylamino)methyl)naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic amines at 90 oC under solvent and catalyst-free conditions. The procedure avoids the use of toxic solvents, tedious work-up, catalyst and purification of the products by chromatographic methods. Simple operation, short reaction times, generating the desired compounds in high to excellent yields and an environmentally benign method are advantages of this protocol.

An Efficient One‐Pot Pseudo Five‐Component Synthesis of Bis‐heteroarylaminomethylnaphthoquinone Mannich Bases from Lawsone

“…In 2016, Mohammadpoor‐Baltork and his co‐workers have published synthesis of symmetric and unsymmetric bis‐aminonaphthoquinones from dialdehyde (terephthaladehyde and isophthalaldehyde) and/or diamines (benzene‐1,4‐diamine and 1,2‐ethylenediamine) in the presence of Fe 3 O 4 @TDSN−Bi(III) in EtOH at room temperature [26] . In continuation of our previous works, reported on synthesis of a new series of lawsone derivatives via one‐pot multi‐component reactions, [27–30] herein we reported the synthesis of a new series of bis‐heteroarylaminomethylnaphthoquinones through one‐pot, multi‐component reactions of lawsone, heteroaryl amines and terephthaldehyde in the presence of a catalytic amount of p ‐TSA in CH 3 CN under reflux conditions.…”

One-Pot and Three-Component Coupling Synthesis of Novel p-[(Benzothiazolylamino)(aryl/heteroaryl)methyl]phenols and Its Corresponding O-Tosylates under Catalyst- and Solvent-Free Conditions

“…Nucleophilic addition of secondary alcohols is the alternate method to synthesize 9H-xanthen-9-yl derivatives, (aminobenzyl)naphthols and (aminobenzyl)phenols by applying acid catalysts. 6 Three-component coupling through Betti reaction 7 has also drawn special attraction as an alternative and straightforward method to introduce the aminobenzothiazole moiety into organic molecules such as coumarins, 8 dibenzofuranol, 9 3hydroxyxanthone, 10 naphthols (1a, Scheme 1), 11 2hydroxynaphthalene-1,4-dione, 12 6 or 8hydroxyquinolines, 13,11b and phenols (1b, Scheme 1) 14 by treating with unsaturated compounds. All these methods provide an amino methyl group at Thus, there is a need to develop a method for para-amino methylation products of phenols by generating both C-C and C-N bonds in a single step.…”