Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones

Abstract

A practical three-component method for the synthesis of pyrazolo[3,4-d]pyrimidin-4-ones was developed.

Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

“…Dolzhenko and co-workers developed a microwave-assisted three-component protocol for the synthesis of pyrazolo[3,4- d ]pyrimidin-4-ones 87a–o. 95 They carried out the microwave-assisted one-pot reaction using methyl 5-aminopyrazole-4-carboxylates 85a–g, trimethyl orthoformate and primary amines 86a–h to afford poor-to-good isolated yields of desired products 87a–o. The reaction mixture was heated at 160 °C for 55 min in ethanolic conditions ( Scheme 30 ).…”

A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones

“…Scheme 2 Reaction of anthranilic acid hydrazide with alkyl 2-cyano-3,3-bis(methylthio)acrylates (6) Expanding molecular diversity of bioactive pyrazolopyrimidinones, reported earlier, 19 we became interested in the pyrazoloquinazolinone scaffold and the development of a new effective method for its construction. Typically, the synthesis of pyrazolo [5,1-b]quinazolinones required heating at high temperatures for a long time.…”

“…17 Recently, an interesting method for the annulation of quinazoline to pyrazoles was developed using a selective acylation of aminopyrazoles with 2-iodobenzoyl chloride followed by intramolecular Goldberg reaction of the resulting 1-(2-iodobenzoyl)-substituted intermediates (Route 9). 18 Expanding molecular diversity of bioactive pyrazolopyrimidinones, reported earlier, 19 we became interested in the pyrazoloquinazolinone scaffold and the development of a new effective method for its construction. Typically, the synthesis of pyrazolo [5,1-b]quinazolinones has required heating at high temperatures for a long time.…”

6-Aryl-4-cycloamino-1,3,5-triazine-2-amines: synthesis, antileukemic activity, and 3D-QSAR modelling

“…9 Recently, we successfully modied the microwave-assisted three-component synthesis of 6,N 2 -diaryl-1,3,5-triazine-2,4-diamines 10 to prepare 6-aryl-4-cycloamino-1,3,5-triazine-2-amines. 11 In continuation of our search for new effective antileukemic agents, 12 we expand herein our method 11 to synthesise a library of 94 diverse 6-aryl-4cycloamino-1,3,5-triazine-2-amines. These compounds were also screened for antiproliferative properties against the Jurkat T cell line (acute T cell leukemia) and a 3D-QSAR model was developed to facilitate further antileukemic drug discovery.…”