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Journal ArticleDOI

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

Ali Khalafi-Nezhad, +2 more
- 01 Jun 2013 - 
- Vol. 96, Iss: 6, pp 1155-1162
TLDR
An efficient one-pot approach to the synthesis of 5,7,8,9,9a,10-hexahydro-8thioxopyrido[2,3-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 as mentioned in this paper.
Abstract
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).

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Citations
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Journal ArticleDOI

Recent applications of barbituric acid in multicomponent reactions

TL;DR: Barbituric acid has been utilized in the design and synthesis of diverse types of heterocyclic and carbcycle-clic compounds and considered as an important building block in organic synthesis as mentioned in this paper.
Journal ArticleDOI

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

TL;DR: 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.
Journal ArticleDOI

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

TL;DR: In this paper, a new class of structurally diverse α-aminophosphonate derivatives containing benzimidazole, theophylline and adenine heterocycles were synthesized using a simple and efficient strategy.
Journal ArticleDOI

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

TL;DR: Results of this study may suggest these synthetic compounds as novel molecular templates for construction of potentially anti-diabetic drugs with the ability for more convenient management of postprandial hyperglycemia.
Journal ArticleDOI

Multicomponent reactions in nucleoside chemistry.

TL;DR: This review covers sixty original publications dealing with the application of multicomponent reactions (MCRs) in the synthesis of novel nucleoside analogs.
References
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Journal ArticleDOI

The application of multi-component reactions in drug discovery

TL;DR: Multi-component reactions enable the facile, automated and high throughput generation of small organic molecules, which provides medicinal chemists with a powerful tool to create novel chemical diversity, matching the space of biological targets with relevant chemistry.
Journal ArticleDOI

Acid catalysis by heteropoly acids

TL;DR: The achievements in the field of acid catalysis by heteropoly acids having different structures HxPW11LO40 (L = ZrIV, TiIV, ThIV), HxZW12O40 (Z = SiIV, PV, BIII, CoIII, GeIV) are reviewed as mentioned in this paper.
Journal ArticleDOI

Tyrosine kinase inhibitors. 15. 4-(Phenylamino)quinazoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of the ATP binding site of the epidermal growth factor receptor.

TL;DR: A series of 6- and 7-acrylamide derivatives of the 4-(phenylamino)quinazoline and -pyridopyrimidine classes of epidermal growth factor receptor (EGFR) inhibitors showed significant tumor growth inhibition (stasis) over a dose range, and the poor aqueous solubility of the compounds was a drawback.
Journal ArticleDOI

Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives.

TL;DR: Semiempirical AM1 calculations showed that negative electrostatic potentials around oxygen of the phenoxy and nitrogen of the imidazole moieties have direct effect on the antibacterial activity towards S. aureus A 15091.
Journal ArticleDOI

Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium

TL;DR: A novel and efficient one-pot synthesis of spiro[indoline-3, 4'-pyrazolo[3,4-b]quinoline]dione, spiro,[furo[3-4-e]pyrazole]dion, and spiro [indeno[2,1-e], pyridine-4,3'-indoline]-dione derivatives via three-component reaction of isatin, 5-amino-3-methylpy
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