Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H‐Pyrano‐[4,3‐b]pyran‐5‐one and 4,6‐Dihydro‐5H‐pyrano‐[3,2‐c]pyridine‐5‐one Scaffolds

Abstract

The general ‘on‐solvent’ PASE approach was found to be medicinally relevant for 4H,5H‐pyrano[4,3‐b]pyran‐5‐one and 4,6‐dihydro‐5H‐pyrano[3,2‐c]pyridine‐5‐one scaffolds. Ammonium acetate‐catalyzed multicomponent reaction of aldehydes and two different C–H acids in the presence of small amounts of EtOH results in fast (3 – 15 min) and efficient formation of scaffolds, promising for many diverse oriented medical applications.

Biomass‐derived Sugar Ionic Liquid as a Sustainable Organocatalyst: An Efficient Synthesis of Functionalized Dihydropyrano Coumarins

“…A plethora of review reports are there on the synthesis of dihydropyrano coumarin derivatives via one pot reaction of aromatic malononitrile, aldehydes and CÀ H active acids in the presence of homogeneous or heterogeneous catalysts such as organic acids or bases, nanoparticles, zeolites, and Ionic liquids. [25][26][27] Numerous catalysts such as 1,4diazabicyclo[2.2.2]octane (DABCO), [11] ammonium acetate, [28] 1,8diazabicyclo[5.4.0]undec-7-ene (DBU), [29] urea, [30] piperzine, [31] triethylbenzylammoniumchloride (TEBA), [32] diammonium hydrogen phosphate, [33] piperidine, [34] ammonium/sodium formate, [35] 2-hydroxyethylammonium formate, [36] CuO, [37] sodium tungstate, [38] Fe 2 O 3 , [39] GN/SO 3 H, [40] oxo-vanadium phthalocyanine, [41] Ti 2 O, [42] cobalt orthophosphate (Co 3 (PO 4 ) 2 ), [43] tert-butyl hydrogen peroxide, [44] cyclodextrin, [45] 1-butyl-3-methylimidazolium triflate [46] and many more have been reported for the synthesis of dihydropyrano coumarins. Yousefi et al prepared pyranocoumarins by employing piperzine as a catalyst (Scheme 1a).…”

Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism

“…In this connection, the PASE approach has recently emerged [5,6], it is based on the Pot economy principle and unites it with the Atom and Step Economy strategies (PASE), thereby ensuring high efficiency, simplicity and low waste formation [7][8][9][10]. Nowadays, it is emerging as a fast-paced research front of organic chemistry [11][12][13][14][15][16].…”

“…, 190 (3), 161(20), 150 (100), 122 (65), 78(16),63 (31), 18(32). HRMS-ESI: [M + H] + , calcd for C 22 H 15 N 6 O 5 443.1104, found 443.1098.…”

An efficient synthesis of 4 H -pyrano quinolinone derivatives catalysed by a versatile organocatalyst tetra- n -butylammonium fluoride and their pharmacological screening

“…Among available methods, intramolecular cyclization via multicomponent reaction is an efficient protocol for the synthesis of new pharmacologically active heterocycles [18]. A literature survey manifests that using this one-pot, threecomponent approach, considerable efforts have been focused on the design and development of environmentally friendly and less expensive procedures for the generation of libraries of heterocyclic compounds employing various catalysts [19][20][21][22][23][24][25][26]. Therefore, the molecular manipulation of the promising lead involves an idea to merge the separate pharmacophoric groups of analogous activity into one compound, hence making structural changes in the biological activity.…”

“….3.2.1. Gram-positive bacteriaAgainst Gram-positive bacteria C. tetani, P 21 (MIC 62.5 µg ml −1 ) was found to have outstanding activity; compounds P 5 , P 7 , P 9 , P 19 , P 20 (MIC 100 µg ml −1 ) showed significant activity; compounds P 4 , P24 (MIC 125 µg ml −1 ) exhibited moderate activity; while compounds P 1 , P 3 , P 11 , P 12 , P 15 , P 17 , P 22 , P 23 (MIC 200 µg ml −1 ) showed better activity; while compounds P 6 , P 8 , P 10 , P 14 , P 15 (MIC 250 µg ml −1 ) were found equally potent when compared with ampicillin (MIC 250 µg ml −1 ). rsos…”