A flexible one-pot synthesis of 8,10-dimethyl-12-aryl-9H-naphto[1′,2′:5,6]pyrano[2,3-d]pyrimidine-9,11-diones catalyzed by ZnO nanoparticles under solvent-free conditions

Abstract

A flexible one-pot synthesis of 8,10-dimethyl-12-aryl-9H-naphto[1 0 ,2 0 :5,6]pyrano[2,3-d]pyrimidine-9,11-diones catalyzed by ZnO nanoparticles under solvent-free conditions Abstract A new, convenient, and green procedure for the synthesis of naphthopyranopyrimidine-diones is described using a one-pot multi-component reaction of b-naphthol, 1,3-dimethylbarbituric acid, and various aryl aldehydes in the presence of ZnO nanoparticles, an effective and recyclable heterogeneous catalyst, under solvent-free conditions. This method provides excellent advantages, such as waste-free, simple work-up procedure, and excellent yield with high selectivity. The stability of the catalyst was investigated by determining its activity after recycling for six times without significant loss of its catalytic activity. Graphical abstract HO N N O O O O N N O O + ZnO NPs 110 o C Ar ArCHO

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

“…Mohaqeq and Ghomi 76 used Lewis acidic ZnO NPs (10 mol %) to synthesize a naphthopyranopyrimidinedione derivative, i.e., 8,10-dimethyl-12-aryl-9 H -naphtho[1′,2′:5,6]-pyrano[2,3- d ]pyrimidinedione 44 by treating discrete 1 (1.1 mmol) with 26 (1 mmol) and 11a (1 mmol) at 110 °C with a lack of solvent, as shown in Scheme 30 . In this regard, Mohaqeq et al 77 synthesized novel analogues of 44a using the same substrates by utilizing heterogeneous catalyst, ZnAl 2 O 4 NPs (0.7 mol %), under microwave irradiation (MWI) of 500 W ( Scheme 30 ).…”

Zinc Oxide Nanoparticles as Efficient Heterogeneous Catalyst for Synthesis of Bio‐active Heterocyclic Compounds

“…M. Mohaqeq and J. S. Ghomi in 2015 reported a greener synthetic tools for the synthesis of naphthopyranopyrimidinedione derivatives [183] when combining β-naphthol (155), 1, 3dimethyl barbituric acid (136), and different aryl aldehydes (4) in a single reactor with ZnO-NPs, an efficient and reusable heterogeneous nanocatalyst under solvent free condition, These types of moieties generated interest in medicinal chemistry because the molecular features of naphthopyranopyrimidine and its derivatives (156) are so beneficial in biological and pharmaceutical chemistry (Scheme 29). This process has several advantages, including no waste, a quick compound separation procedure, and a high yield with great selectivity.…”

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

“…A common route for the synthesis of benzo [5,6]chromeno [2,3-d]pyrimidine derivatives is a three-component coupling reaction of naphthols, aldehydes and barbituric acid/1,3-dimethylbarbituric acid/thiobarbituric acid/1,3-dimethyl-2-thiobarbituric acid/6-amino-1,3dimethyluracil. To date, various conditions have been applied to promote this reaction in the presence of both homogeneous and heterogeneous catalysts such as InCl 3 , [12] I 2 , [13] KAl(SO 4 ) 2 .12H 2 O, [14] sulfated tin oxide, [15] HCOOH, [16] Lactic acid, [17] potassium phthalimide-N-oxyl (PPINO), [18] p-TSA, [19] cetylpyridinium chloride (CPC), [20] HClO 4 -SiO 2 , [21] H 3 PO 4 /Al 2 O 3 , [22] ZnO, [23] ([HMIm][HSO 4 ]) or Fe 3 O 4 @MCM-48-SO 3 H, [24] ZrOCl 2 /nano-TiO 2 , [25] cellulose sulfuric acid, [26] ZnAl 2 O 4 , [27] perlite NPs@IL/ ZrCl 4 , [28] MWCNTs@NHBut/PTA, [29] LaMo 0.1 Fe 0.9 O 3 , [30] PATDBP)(HSO 4 ) 2 @HNT, [31] MWCNTs@SiO 2 /MSA, [32] Nd 2 O 3 @g-C 3 N 4 , [33] H 4 [SiW 12 O 40 ], [34] L-proline, [35] and Al(H 2 PO 4 ) 3 . [36] Recently, one review article has been published based on the synthesis of naphthopyranopyrimidine derivatives.…”