Succinimide-N-sulfonic acid as an efficient recyclable catalyst for the synthesis of some fused indolo pyrano pyrimidinone derivatives

Abstract

ABSTRACT.A new, simple, thermally efficient and solvent-free condensation of 2-amino-4,5-dihydro-4-phenylpyrano[3,2-b]indole-3-carbonitrile derivatives with coumarin-3-carboxylic acid employing succinimide-Nsulfonic acid (SuSA) as catalyst for the synthesis of a series of 5,6-dihydro-2-(2-oxo-2H-chromen-3-yl)-5-phenylindolo[2',3':5,6]pyrano[2,3-d]pyrimidin-4(3H)-one derivatives is described. This method has the advantages of high yield, simple methodology, and short reaction time, as well as being green in terms of avoiding the use of toxic catalysts and solvents. Furthermore, the catalyst could be recycled and reused four times without significant loss of activity. Thiourea dioxide (TUD) catalyzed efficient three-component coupling reactions of aromatic aldehydes, 3-hydroxyindole and malononitrile in water at 70 ºC was described as the preparation of 2-amino-4,5-dihydro-4-phenylpyrano[3,2-b]indole-3-carbonitrile derivatives.

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

“…Polyhydroquinoline derivatives 79 were prepared by treatment of aldehydes 1 , diketone or β‐ketoester 3 , dimidone 72 or 1,3‐cyclohexanedione 72a , and ammonium acetate under different reaction conditions (Methods A‐Q, Scheme , Table ) …”

Efficient synthesis of β‐aminoketones catalyzed by Fe3O4@ quillaja sapogenin/Ni (II) as a novel magnetic nano‐catalyst

“…Catalyst Amount Temperature ( C) Time(h) yield (%) [b] Ref 1 BiNO 3 10 mol% 25 4 89 [24] 2 Diaryliodonium (III) 10 mol% 25 24 83 [23] 3 Saccharose 15 mol% 25 9 92 [45] 4…”

“…Compounds of the β-aminoketones, which are necessary intermediates in herbal products, were provided through the mentioned process. [17,20] Previously, a portion of the β-aminoketone's compounds had already been catalyzed by H 3 PW 12 O 30 (hetero poly acids), [21] carbon-based solid acid, [22] diaryliodonium (III), [23] BiNO 3 , [24] citric acid, [25] proline and solution, [26,27] calixarenes, [28] Cu/NH 2 -SBA-15,, [29] InCl 3 [30] ionic liquid (carboxyl-functionalized poly) (CFPIL). [31] The mentioned catalysts for this purpose, despite having some advantages, have also some disadvantages, including time consuming reaction process, a small yield of products, harmfulness, and low efficiency in the recovery process.…”

Contemporary development in sequential Knoevenagel, Michael addition multicomponent reaction for the synthesis of 4-Aryl-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile

“…A number of homogeneous as well as heterogeneous catalysts [57][58][59][60][61][62][63][64][65][66][67][68] have been employed for the preparation of pyridines, dihydropyridines, and its analogs in diverse methods, e.g. acid [69,70], base [71,72], microwave synthesis [58], ionic liquid [73,74], etc., are cited in literature, but they have their own merits and demerits. It has been evidenced that in most of the cases, the synthesis of the N-containing skeleton is carried out by using ammonium salts as an N-source, but in the absence of an ammonium salt, aromatic aldehyde, malononitrile, and 1,3-diketone react to give a pyran derivative [75][76][77].…”