Organocatalytic clean synthesis of densely functionalized 4H-pyrans by bifunctional tetraethylammonium 2-(carbamoyl)benzoate using ball milling technique under mild conditions

Abstract

A green and simple method has been developed for efficient preparation of diverse annulated 2-amino-3-cyano-4H-pyran derivatives in the presence of a low loading of tetraethylammonium 2-(carbamoyl)benzoate (TEACB), as a bifunctional organocatalyst, under solvent-free conditions using the ball milling technique. This procedure is a clean, transition-metal-free, and environmentally friendly approach that offers many advantages including short reaction times, high to quantitative yields, low cost, and straightforward work-up. ARTICLE HISTORY

Trimesic acid-functionalized chitosan: A novel and efficient multifunctional organocatalyst for green synthesis of polyhydroquinolines and acridinediones under mild conditions

“…In addition, there are several positive aspects for using of heterogeneously-catalyzed processes including simplification of procedures, assistance to decreasing trend of the waste production, and easy separation and recycling of the catalysts [ [12] , [13] , [14] ]. Interestingly, these biomaterials are environmentally-friendly alternative supports for other materials such as diverse synthetic organic polymers [ [15] , [16] , [17] , [18] ], metal organic frameworks (MOFs) [ 19 , 20 ], graphene-oxide or its reduced form [ [21] , [22] , [23] ], alumina [ 24 ], silica, zeolites or their magnetic composites [ 16 , [25] , [26] , [27] , [28] , [29] ], which can be used to stabilize active catalytic agents onto the surface of the supports as well as tune desired catalytic activities.…”

Copolyesters of ε-caprolactone and l-lactide catalyzed by a tetrabutylammonium phthalimide-N-oxyl organocatalyst

“…35 The air/moisture-tolerant tetrabutylammonium phthalimide-N-oxyl (TBAPINO), synthesized with cheap raw materials, have found applications in cyanosilylation of carbonyl compounds, cyclotrimerization of aryl and alkyl isocyanates, etc. [36][37][38] Our previous work has proved its excellent catalytic efficiency towards ROP of L-LA both in bulk and solution polymerization. 39 Therefore, in present work, we expanded the application of TBAPINO and further described the catalytic activity towards ROP of 3-CL (Fig.…”

The Investigation of Michael Addition of Acetoacetanilide and Methyl Acetopyruvate to Some Ylidenecyanoacetamides

“…Antibacterial, spazmolitical, diuretic, anticoagulyant, antidiabetic, anticancer və antianaphilactic and other various pharmacological properties of quinazolines, 3,4-dihydropyrdine-2-one and 2-amino-4H-pyrane derivatives were investigated [8][9][10].…”