Agar-entrapped sulfonated DABCO: Agelly acidic catalyst for the acceleration of one-pot synthesis of 1,2,4-triazoloquinazolinone and some pyrimidine derivatives

Abstract

Highlights Structurally functionalized 1,2,4-triazoloquinazolinone and some pyrimidine derivatives were synthesized by agar-entrapped sulfonated DABCO as a non-metal catalyst. The moisture-resistant property of the catalyst were investigated. A simple purification step was performed to achieve high purity. The reusability of the catalyst was investigated during three runs for all compounds.

Nano-[Fe3O4@SiO2/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl2] as a nano magnetite Schiff base complex and heterogeneous catalyst for the synthesis of pyrimido[4,5-b]quinolones

“…In a proposed mechanism which is supported by the literature, [17][18][19][20][21][22][23][24]44 in the rst step, dimedone in enole form was reacted with activated aldehyde by the catalyst to give (I) and then by removing of one molecule of H 2 O, intermediate (II) as an Michael acceptor was prepared. In the next step, by the reaction of 6-amino-1,3-dimethyluracil with (II), which was activated by the catalyst, (III) was obtained.…”

“…1 Multi-component reactions are one of the most successful methods in organic chemistry to increase the structural diversity and molecular complexity using a simple process without the formation of side-products and save energy, time, solvent and chemical materials and reduce the chemical waste. [10][11][12][13][14][15][16] Multi-component reaction of aryl aldehyde, dimedone and 6-amino-1,3dimethyluracil is carried out by various catalysts including nano-[Fe 3 O 4 @-SiO 2 @R-NHMe 2 ][H 2 PO 4 ], 1 SBA-15/PrN(CH 2 PO 3 -H 2 ) 2 , 17 [TSSECM], 18 Fe 3 O 4 @cellulose sulfuric acid, 19 Agarentrapped sulfonated DABCO, 20 [C 4 (DABCO) 2 ]$2OH, 21 nanocrystalline MgO, 22 [H 2 -DABCO][ClO 4 ] 2 (ref. 23) and [bmim]Br.…”

Synthesis of Novel Pyrimido[4,5-b] Quinolines Containing Benzyloxy and 1,2,3-Triazole Moieties by DABCO as a Basic Catalyst

“…In a mechanism which is supported by the previous literature, − dimedone converts into the enol form by the tautomerization and then DABCO attracted one proton from the hydroxyl group to obtain 5,5-dimethyl-3-oxocyclohex-1-enolate. In the next step, the prepared enolate attacked to aldehyde which is activated by protonated DABCO and lost a molecule of water to generate ( I ) as an intermediate.…”

“…According to the importance of the mentioned pyrimido­[4,5- b ]­quinolines, various catalysts were reported for the multi-component synthesis of pyrimido­[4,5- b ]­quinolines such as [TSSECM], SBA-15/PrN­(CH 2 PO 3 H 2 ) 2 , [H 2 -DABCO]­[ClO 4 ] 2 , nano-[Fe 3 O 4 @SiO 2 / N -propyl-1-(thiophen-2-yl)­ethanimine]­[ZnCl 2 ], nano-[Fe 3 O 4 @-SiO 2 @R-NHMe 2 ]­[H 2 PO 4 ], Fe 3 O 4 @Cellulose sulfuric acid, N , N -diethyl- N -sulfoethanaminium chloride, [bmim]­Br, glycolic acid-supported cobalt ferrite, nanocrystalline MgO, [C 4 (DABCO) 2 ]·2OH, and agar-entrapped sulfonated DABCO . However, most of the proposed methods are performed by acidic and expensive catalysts.…”

“…According to the importance of the mentioned pyrimido[4,5- b ]quinolines, various catalysts were reported for the multi-component synthesis of pyrimido[4,5- b ]quinolines such as [TSSECM], 1 SBA-15/PrN(CH 2 PO 3 H 2 ) 2 , 23 [H 2 -DABCO][ClO 4 ] 2 , 24 nano-[Fe 3 O 4 @SiO 2 / N -propyl-1-(thiophen-2-yl)ethanimine][ZnCl 2 ], 25 nano-[Fe 3 O 4 @-SiO 2 @R-NHMe 2 ][H 2 PO 4 ], 26 Fe 3 O 4 @Cellulose sulfuric acid, 27 N , N -diethyl- N -sulfoethanaminium chloride, 28 [bmim]Br, 29 glycolic acid-supported cobalt ferrite, 30 nanocrystalline MgO, 31 [C 4 (DABCO) 2 ]·2OH, 32 and agar-entrapped sulfonated DABCO. 33 However, most of the proposed methods are performed by acidic and expensive catalysts. A suitable basic catalyst for the synthesis of these valuable compounds has not yet been proposed.…”