An efficient one pot three-component synthesis of dihydropyrano[3,2-c] chromenes using ammonium metavanadate as catalyst

Abstract

We report ammonium metavanadate catalyzed one-pot synthesis of 3,4-dihydropyrano[3,2c]chromenes, from aldehydes, active methylene compounds malononitrile and 4hydroxycoumarin in water:ethanol(1:1) under reflux. The attractive features of this process are mild reaction conditions, short reaction times, easy isolation of products, and excellent yields.

Synthesis and characterization of an Fe-MOF@Fe3O4 nanocatalyst and its application as an organic nanocatalyst for one-pot synthesis of dihydropyrano[2,3-c]chromenes

“…As a major heterocyclic chromene, dihydropyrano[2,3- c ]chromene can be obtained by Knoevenagel cyclocondensation of malononitrile, 4-hydroxycoumarin, and aldehydes. Regarding the widespread application of such compounds, different approaches have been developed for this reaction, including catalyst and reagent diversity, heterogeneous and homogeneous catalysts, ultrasonic and microwave irradiation ( Tu et al, 2003 ; Kidwai and Saxena, 2006 ), pyridine/piperidine in ethanol ( Shaker, 1996 ), electrolysis ( Fotouhi et al, 2007 ), ChOH (choline hydroxide) ( Zhu et al, 2015 ), SDS (sodium dodecyl sulfate), TBAB (tetrabutylammonium bromide) ( Khurana and Kumar, 2009 ), TMGT (tetramethylguanidinium trifluoroacetate) ( Shaabani et al, 2005 ), Na 2 SeO 4 ( Hekmatshoar et al, 2008 ), CuO, MgO, a -Fe 2 O 3 , ZnO, and Al 2 O 3 nanoparticles ( Nagabhushana et al, 2011 ; Montaghami and Montazeri, 2014 ), ZIF@ZnTiO 3 organocatalysts ( Farahmand et al, 2019 ), Fe 3 O 4 magnetic nanoparticles ( Ezzatzadeh et al, 2017 ), urea ( Brahmachari and Banerjee, 2014 ), supported ionic liquids ( Sharma et al, 2016 ), starch solutions ( Hazeri et al, 2014 ), NH 4 VO 3 ( Shitole et al, 2016 ), ammonium acetate ( Kanakaraju et al, 2017 ), grindstone chemistry ( Patel et al, 2016 ), mefenamic acid ( Asadpour B et al, 2020 ), and iron ore pellets ( Sheikhhosseini et al, 2016 ), as well as other catalysts. Novel techniques have to be developed to overcome the disadvantages of previous approaches.…”

Dual Copper (II) Complex Supported on Diatomite as a Novel and Green Catalyst for the Synthesis of Dihydropyrano[3;2‐b]Chromenediones and Aminopyranopyrans

“…Different catalysts were reported for these reactions, including palladium catalyst, [17] pyridinium-based salts, [18] Bi(OTf) 3 , [19] Fe 3 O 4 @SiO 2 , [20] magnetic ionic liquid, [21] CeCl 3 ⋅ 7H 2 O/SiO 2 , [22] ultrasonic irradiation, [23] Fe 3 O 4 @SiO 2 -AQ, [24] urea-based catalysts, [25] bifunctional tertiary amin [26] and NH 4 VO 3. [27] However, despite the efficiency of these methods, the development of less expensive and environmentally benign reaction conditions is a major goal for the synthesis of pyranopyran and chromene derivatives. Therefore, the development of efficient, convenient, environmentally benign, and recyclable catalyst is essential.…”

A Green and Efficient Method for the Synthesis of 3,4- Dihydropyrano[c]chromene using Phosphate Fertilizers (MAP, DAP and TSP) as Heterogeneous Catalysts

“…Following the importance and usefulness of dihydropyrano[c]chromene derivatives, numerous synthetic pathways have been described, including electrolysis (24) microwave and ultrasonic irradiation (25)(26) by piperidine/pyridine in ethanol (27), H6P2W18O62 • 18H2O, tetrabutylammonium bromide, copper oxide nanoparticles, sodium dodecyl sulfate (SDS), trisodium citrate, selectfluor chloride triethylbenzylammonuim DABCO in aqueous media (28)(29)(30)(31)(32)(33)(34)(35). Tetramethylguanidinium trifluoroacetate (TMGT) (36), rare earth perfluorooctanoates (37), Na2SeO4 (38), SiO2-Pr-SO3 (39), functionalized sulfonic acid silica (40), hexamethylenetetramine (41), Fe2O3 nanoparticles (42), the complexes of silica gel (43), Ru (II) (44), Urea (45), NH4VO3 (46), starch solution (47), grindstone chemistry (48), SBPPSP (49), MgO nanoparticle (50), ammonium acetate (51), 4-(dimethylamino)pyridine (DMAP) (52). Some synthetic catalysts of phosphate have also been reported in the literature for 3,4-dihydropyrano[c]chromenes synthesis; one found the Disodium hydrogen phosphate (53) and DHAP which has been described once as a homogeneous catalyst in the presence of ethanol-water (54).…”