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

Abstract

A new series of bis‐heteroarylaminomethylnaphthoquinone Mannich bases have been synthesized through facial and efficient one‐pot pseudo five‐component reactions of lawsone, different heteroaryl amines and terephthaldehyde using p‐TSA as catalyst in CH3CN under reflux conditions. The high yields of products, very simple operation, readily available starting materials, high atom‐economy, easy workup procedure and isolation/purification of target products without chromatography are the main benefits of this synthetic strategy.

Recent Advances in the Synthesis of 2-Hydroxy-1,4-naphthoquinone (Lawsone) Derivatives

“…This synthetic approach offers several advantages, such as high product yields, easy operation, high atom-economy, simple workup procedure, and the ability to isolate/purify target products without chromatography (Scheme 80). 108 Scheme 80 Bis-heteroaryl-aminomethylnaphthoquinone derivatives 260a-f.…”

“…Olyaei et al 108 developed a facile and effective one-pot, pseudo-five-component reaction utilizing p -TSA as a catalyst in CH 3 CN under reflux conditions, to produce a series of bis-heteroarylaminomethylnaphthoquinones 260a – f Mannich bases. Lawsone ( 1 ), various heteroaryl amines 259a – f , and terephthalaldehyde ( 258 ) were employed as readily available starting materials.…”

Acid‐Mediated One‐Pot Three‐Component Tandem Cyclization: Access to Some New Series of Benzo[5,6]chromeno[2,3‐d]pyrimidine Derivatives

“…[37] However, development of convenient and atom-economic protocols for synthesis of naphthopyranopyrimidines is still of high importance in context of modern organic and medicinal chemistry. In continuation of our previous efforts regarding the synthesis of organic compounds based upon MCRs, [38][39][40][41][42][43][44][45] for the first time herein, we describe a convenient synthetic approach for the synthesis of some new series of benzo [5,6]chromeno [2,3d]pyrimidine derivatives by the one-pot, three-component reaction of 2,3-dihydroxynaphthalene, 2-thiobarbituric acid and aromatic aldehydes using sulfuric acid as catalyst in glacial acetic acid under reflux conditions.…”