One-pot synthesis of annulated pyrido[2,3-d:6,5-d]dipyrimidine derivatives using nitrogen based DBU catalyst in aqueous ethanol medium

Bhat, Ajmal R.; Dongre, Rajendra S.

doi:10.1016/j.jtice.2015.04.020

Cited by 21 publications

(9 citation statements)

References 25 publications

(18 reference statements)

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“…66 The Dongre group demonstrated a simple and environmentally benign approach for the one-pot threecomponent preparation of various of annulated pyrido[2,3-d:6,5-d]dipyrimidine derivatives (26) through the three-component cyclocondensation of aromatic aldehyde (1), thiobarbituric acid (24), and 6-aminouracil (2) catalyzed by DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as an efficient organocatalyst in aqueous ethanol under reflux (Scheme 14). 67 This methodology offered various benefits like excellent yields, short reaction time, environment-friendly procedure, easy isolation of products, and excellent yields (72-89%). DBU is one of the most substantial organocatalysts bases (pKa = 12), which has been used for various organic syntheses due to its cheap, readily available, environmentally friendly, highly active, and non-toxic nitrogen-base catalysts.…”

Section: © Author(s)mentioning

confidence: 99%

“…One-pot synthesis of pyrido[2,3-d:6,5-d]dipyrimidinec derivatives using DBU. 67 A clean and practical three-component synthesis of fused indenopyridines (27) containing an uracil moiety from benzaldehydes (1), 6-aminouracils (2), and 2-bromo-1H-indane-1,3(2H)-dione (27) was developed by Bazgir and co-workers in the presence of ammonium acetate in HOAc under reflux conditions. They found that acetic acid is the most suitable reaction media (Scheme 15).…”

Section: © Author(s)mentioning

confidence: 99%

“…Brahmachari and Banerjee reported a simple, facile, and convenient, practical method for the one-pot synthesis of biologically relevant alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (67). (Scheme 40).…”

Section: Synthesis Of 6-aminouracil Arylmethane Derivativesmentioning

confidence: 99%

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Recent applications of aminouracil in multicomponent reactions

Javahershenas¹

2021

Arkivoc

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6-Aminouracil and its derivatives are versatile heterocyclic compounds and are frequently employed to synthesize a wide array of fused uracils annulated with other heterocyclic rings which can serve to address biological and pharmacological targets. Multicomponent reactions (MCRs) are important in the synthesis of natural products and pharmaceuticals by forming heterocyclic molecular frameworks with generally high atom-economy in a single reaction step. This review embraces various modern synthetic strategies, summarizing recent research developments providing fused 6-aminouracil derivatives and to highlight the progress based on MCRs between 2015 and 2020.

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Section: © Author(s)mentioning

confidence: 99%

Section: © Author(s)mentioning

confidence: 99%

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Recent applications of aminouracil in multicomponent reactions

Javahershenas¹

2021

Arkivoc

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“…Reaction of aldehyde with aminouracil or dimethyl aminouracil 67 and barbituric acid derivatives 94 under different conditions (Methods A and B) afforded pyrido[2,3‐ d :6,5‐ d ′]dipyrimidine derivatives 152 in good yields (Methods A and B, Scheme , Table ) …”

Section: Synthesis Of Fused Tricyclic Systemmentioning

confidence: 99%

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

Abdella

Abdelmoniem

Abdelhamid

et al. 2020

Journal of Heterocyclic Chem

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Heterocycles represent the largest diversity of organic compounds with signifcant chemical, biomedical, and industrial applications. They exist in numerous natural products, dyes, and as scaffolds in diverse drugs and related pharmaceutically active substances. Substantial attention has been paid to develop various elegant methods to synthesize heterocycles. Among different strategies, Michael and Hantzsch reactions are considered as effective approaches for construction of heterocycles and their corresponding fused derivatives. This review covers this area especially in the last 10 years. The heterocyclic systems reported in this review are classified according to the kind of the heterocyclic systems.

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“…Literature surveys revealed that there are a number of methods for the synthesis of N 10 -unsubstituted 9,10-dihydropyrido[2,3- d :6,5- d ′]dipyrimidine-2,4,6,8(1 H ,3 H ,5 H ,7 H )-tetraones using a variety of catalysts such as DBU, SBA-15-SO 3 H, [H-NMP] + [HSO 4 ] − , γ-Fe 2 O 3 @HAp-SO 3 H, nano-CuFe 2 O 4 , − nano-Fe 3 O 4 , and these protocols required the use of organic solvents, heating, and/or refluxing, microwave irradiation, and ultrasound irradiation. However, syntheses of N 10 -substituted dihydropyrido[2,3- d :6,5- d ′]dipyrimidines were reported only by the research group of Khalafi-Nezhad from the three-component condensation reaction of barbituric acids, anilines, and aromatic aldehydes or sugars upon refluxing the reactants in ethanol either in the presence of phosphotungstic acid (TPA) or p -toluenesulfonic acid or magnetic nanoparticle-supported tungstic acid (MNP-TA) as the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Development of a Water-Mediated and Catalyst-Free Green Protocol for Easy Access to a Huge Array of Diverse and Densely Functionalized Pyrido[2,3-d:6,5-d′]dipyrimidines via One-Pot Multicomponent Reaction under Ambient Conditions

Brahmachari

Nurjamal

Karmakar

et al. 2017

ACS Sustainable Chem. Eng.

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A water-mediated and catalyst-free simple protocol for easily accessing a huge array of pharmaceutically interesting and diversely functionalized 5-alkyl/aryl/heteroaryl-10-alkyl/aryl-2,8-dioxo/dithioxo-9,10-dihydropyrido[2,3d:6,5-d′]dipyrimidine-4,6(1H,3H,5H,7H)-dione derivatives 4 (4-1−4-42) and 5,5′-(1,4-phenylene)bis(10-alkyl/aryl-2,8dioxo/dithioxo-9,10-dihydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,3H,5H,7H)-dione) 4′ (4′-1−4′-8) has been developed based on a one-pot multicomponent reaction between barbituric/N,N-dimethylbarbituric/2-thiobarbituric acids (1), substituted amines (2), and aldehydes (3) under ambient conditions. The salient features of this protocol are the clean reaction profile, use of no added catalyst, water as reaction media, mild reaction conditions at room temperature, energyefficiency, easy isolation of products, no need of column chromatographic purification, high atom-economy and low E-factor, good to excellent yields, and reusability of reaction media.

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One-pot synthesis of annulated pyrido[2,3-d:6,5-d]dipyrimidine derivatives using nitrogen based DBU catalyst in aqueous ethanol medium

Cited by 21 publications

References 25 publications

Recent applications of aminouracil in multicomponent reactions

Recent applications of aminouracil in multicomponent reactions

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

Development of a Water-Mediated and Catalyst-Free Green Protocol for Easy Access to a Huge Array of Diverse and Densely Functionalized Pyrido[2,3-d:6,5-d′]dipyrimidines via One-Pot Multicomponent Reaction under Ambient Conditions

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