The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones
نویسندگان
چکیده
The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to N-(bromoalkyl)phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms.
منابع مشابه
Synthesis, X-Rays Analysis, Docking Study and Cholinesterase Inhibition Activity of 2,3-dihydroquinazolin-4(1H)-one Derivatives
In search of potent cholinesterase inhibitors, we have carried out the synthesis and biologically evaluation of various benzaldehyde based 2,3-dihydroquinazolin-4(1H)-one derivatives. In vitro assay results revealed that all the synthesized compounds showed activity against both enzymes (AChE and BChE) and in few cases, the inhibition activity was even higher than or comp...
متن کاملZrP2O7 nanoparticles as a robust and efficient catalyst for the synthesis of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones under microwave irradiation
ZrP2O7 nanoparticles have been used as an efficient catalyst for the preparation of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones by a simple one-pot four-component reaction of phenyl hydrazines, ethyl acetoacetate ,β-naphthol and benzaldehydes under microwave irradiation in good to excellent yields. When the reaction was carried out using ZrOCl2.8H2O, ZrO2 and ZrP2O7 NPs as the catalyst, the pr...
متن کاملSynthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst
Nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst have been used for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates by the four component reaction of dimethylacetylenedicarboxylate, hydrazinehydrate, malononitrile and aromatic aldehydes in water at room temperature. In this research Nano-ZnZr4(PO4)6 coordinate with the active groups(...
متن کاملSynthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst
Nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst have been used for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates by the four component reaction of dimethylacetylenedicarboxylate, hydrazinehydrate, malononitrile and aromatic aldehydes in water at room temperature. In this research Nano-ZnZr4(PO4)6 coordinate with the active groups(...
متن کاملChloroacetic acid-promoted heterocyclic reactions: Efficient preparation of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones
Facile and versatile procedures have been explored for the synthesis of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones. These protocols employ the one-pot multi-component condensation of arylaldehydes and aromatic amines with β-keto esters and isatoic anhydride in chloroacetic acid, respectively. The reactions proceeded smoothly to generate the corresponding products in high yield. We...
متن کامل