M. Mohammadnejad, M. Hashtroudi, S. Balalaie
Dec 1, 2009
Citations
0
Influential Citations
3
Citations
Journal
Heterocyclic Communications
Abstract
One-pot three component condensation of Meldrum's acid, benzaldehyde derivatives and guanidinium carbonate leads to 2-amino-6-aryl-5,6-dihydro-3//-pyrimidin-4-one derivatives in good yields. The products can be utilized in the synthesis of diverse heterocyclic compounds libraries. Introduction Known heterocycles dihydropyrimidines (DHPMs) represent a heterocyclic system of remarkable pharmacological efficiency, and may exhibit antiviral, antitumor, antimicrobial and anti-inflammatory properties. Several marine natural products containing the DHPM core were found to be potent HIVgp-120-CD4 inhibitors. Some 2-aminoDHPMs were found as novel 5-HT5A-receptor in the limbic brain areas suggests a potential role in the modulation of psychiatric diseases. There are some reports for the synthesis of 2-amino DHPMs. The reported methods are as follows: a) Reaction of active methylene compounds, aldehyde and guanidine. b) Using of resin-bound isothiourea building blocks and multidirectional resin cleavage. c) Cyclization of 3-guanidinocarboxylic acids by refluxing in hydrochloric acid media. However, the most general known route to 2-amino-DHPMs is condensation of ß-keto esters with guanidine. All the approaches are quite laborious and prolonged; they require initial synthesis of starting materials and give relatively low overall yields. Recently, Gorobets et al. reported three component condensation of Meldrum's acid, benzaldehydes and guanidine under conventional and microwave conditions. Following of our research work about one-pot multicomponent reactions in recent two years, we concentrated on the new Domino Knoevenagel-Michael condensation. In the present work, we report a new three-component reaction of Meldrum's acid, aromatic aldehyde and guanidinum carbonate that provides an easy access to 2-amino-6-aryl-5,6dihydro-3H-pyrimidin-4-one(2-NH2-DHPMs) building blocks under reflux condition.