Barbituric acid has been utilized in the design and synthesis of diverse types of heterocyclic and carbocyclic compounds and considered as an important building block in organic synthesis. There is a wide range of multicomponent reactions that include barbituric acid as starting material. This article aims to review the chemistry of barbituric acids employed in the design and synthesis of different types of compounds during the period from 2011 to 2015.

Recent applications of barbituric acid in multicomponent reactions

In this study, L-cysteine was chemically grafted to magnetic nanoparticles in order to prepare a reusable magnetic material incorporating an amino acid moiety. For this purpose, silica-coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane to produce vinyl-functionalized magnetic nanoparticles (VMNP). Reaction of a VMNP substrate with L-cysteine in the presence of azobisisobutyronitrile (AIBN) resulted in the production of L-cysteine-functionalized magnetic nanoparticles (LCMNP). The LCMNP material was characterized using different microscopy and spectroscopy techniques such as FT-IR, XRD, TEM, SEM, EDX, VSM, and elemental analysis. Also, LCMNP was analyzed by thermogravimetric analysis (TGA) in order to determine its thermal behavior. The applicability of the LCMNP material was evaluated in a three-component coupling reaction between a nucleophile, salicylaldehyde and malononitrile as the catalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives. The catalyst system showed high catalytic activity in this process and target products were obtained in high isolated yields in water as a green solvent. The LCMNP catalyst was reusable in this reaction at least 7 times with no significant decrease in its catalytic activity.

L-cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water.

A new class of structurally diverse α-aminophosphonate derivatives containing benzimidazole, theophylline and adenine heterocycles were synthesized using a simple and efficient strategy. This class of α-aminophosphonates was synthesized using the reaction of synthetic aldehydes containing nucleobases, amines and diethyl phosphonate using L-cysteine functionalized magnetic nanoparticles (LCMNP) as catalyst. The aldehyde derivatives containing benzimidazole, theophylline and adenine nucleobases were synthesized using the reaction of a bromo-substituted aldehyde derived from isovanillin and 4-hydroxy benzaldehyde. The LCMNP catalyst was found to be an efficient magnetic reusable catalyst for synthesis of this class of α-aminophosphonates under mild and clean conditions. This method is introduced as a suitable approach for the synthesis of new α-aminophosphonate derivatives containing nucleobases which have potential biological activity. When the anticancer properties of a selected group of these synthetic ligands were evaluated, they indicated poor activity compared to cisplatin against the Jurkat cancer cell line.

Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using L-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties

Synthesis of novel poly-hydroxyl functionalized acridine derivatives as inhibitors of α-Glucosidase and α-Amylase.

This review covers sixty original publications dealing with the application of multicomponent reactions (MCRs) in the synthesis of novel nucleoside analogs. The reported approaches were employed for modifications of the parent nucleoside core or for de novo construction of a nucleoside scaffold from non-nucleoside substrates. The cited references are grouped according to the usually recognized types of the MCRs. Biochemical properties of the novel nucleoside analogs are also presented (if provided by the authors).

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-10-179.pdf

Multicomponent reactions in nucleoside chemistry.

An efficient one-pot approach to the synthesis of 5,7,8,9,9a,10-hexahydro-8-thioxopyrido[2,3-d : 6,5-d′]dipyrimidine-2,4,6(1H,3H,5aH)-triones 5 via a four-component reaction of an aldehyde 1, an amine 2, a barbituric acid 3, and thiouracil (4) is reported for the first time. This new multicomponent reaction is accomplished in refluxing EtOH in the presence of tungstophosphoric acid (H3PW12O40) as a catalyst. A variety of hexahydropyrido[2,3-d : 6,5-d′]dipyrimidinetrione derivatives were successfully synthesized in excellent yields with this protocol (Table 2).

One‐Pot Synthesis of 5,7,8,9,9a,10‐Hexahydro‐8‐thioxotetrahydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6(1H,3H,5aH)‐triones via a Four‐Component Coupling Reaction of Aldehydes, Amines, Barbituric Acids, and Thiouracil

One‐Pot Synthesis of 5,7,8,9,9a,10‐Hexahydro‐8‐thioxotetrahydropyrido [2,3‐d:6,5‐d′]dipyrimidine‐2,4,6(1H,3H,5aH)‐triones via a Four‐Component Coupling Reaction of Aldehydes, Amines, Barbituric Acids, and Thiouracil.

Bahman Golesorkhi

Papers

One‐Pot Synthesis of 5,7,8,9,9a,10‐Hexahydro‐8‐thioxotetrahydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6(1H,3H,5aH)‐triones via a Four‐Component Coupling Reaction of Aldehydes, Amines, Barbituric Acids, and Thiouracil

One‐Pot Synthesis of 5,7,8,9,9a,10‐Hexahydro‐8‐thioxotetrahydropyrido [2,3‐d:6,5‐d′]dipyrimidine‐2,4,6(1H,3H,5aH)‐triones via a Four‐Component Coupling Reaction of Aldehydes, Amines, Barbituric Acids, and Thiouracil.