One-pot Green Synthesis for Pyrimido[4,5-d]pyrimidine Derivatives

Kidwai, Mazaahir; Singhal, Kavita; Kukreja, Shuchi

doi:10.1515/znb-2007-0518

Cited by 33 publications

(11 citation statements)

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“…A practically convenient and eco-friendly aqua mediated synthesis of pyrimido [4,5-d]pyrimidines by the reaction of barbituric acid, aldehyde and urea or thiourea to yield pyrimido [4,5-d]pyrimidines has been developed by Kidwai et al [11] without using any catalyst and hazardous organic solvents and corrosive acids or bases. Water-insoluble solid products obtained in short time are found to be essentially pure and in very high yield (Figure 4).…”

Section: Synthesis Of Pyrimido[45-d]pyrimidine [11]mentioning

confidence: 99%

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2017

MOJBOC

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Section: Synthesis Of Pyrimido[45-d]pyrimidine [11]mentioning

confidence: 99%

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2017

MOJBOC

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“…Similarly, pyrimido [4,5-d]pyrimidine derivatives 147 were synthesized by reaction of aldehyde 2, barbituric acid 146 and urea/thiourea using either solid support of alumina 107 or water 108 under microwave irradiation (Scheme 52).…”

Section: Scheme 51mentioning

confidence: 99%

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

Abdel‐Wahab¹,

Khidre²,

Farahat³

et al. 2012

Arkivoc

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This review summarizes the synthetic methods, reactions and biological applications of 2-chloroquinoline-3-carbaldehydes during the period from 1999 to 2011. The reactions are subdivided in groups that cover reactions at the chloro or aldehyde substituent and reactions which involve both groups. Most reaction types have been successfully applied and used in the production of biological active compounds.Keywords: Vilsmeier-Haack reaction, quinolines, aldehydes IntroductionInteresting pharmacological properties have been associated with 2-chloroquinoline-3-carbaldehydes and their derivatives.1,2 These compounds have shown antimicrobial, [1][2][3] antimalarial, 4,5 anti-inflammatory, 6-9 antitumor, 10,11 and anti-parasitic activity. 12 Despite this versatile importance, and in connection to our previous review articles about biologically active heterocyclic systems, 13 2-chloroquinoline-3-carbaldehydes have not been previously reviewed.The main objective of the present survey is to provide the synthesis, reactions, and biological applications of 2-chloroquinoline-3-carbaldehydes from 1999 to the end of 2011 and provide useful and up-to-date data for organic and medicinal chemists. Synthetic MethodsThere have been a number of practically important routes to synthesise of 2-chloroquinoline-3-carbaldehydes, e.g. (i) Vilsmeier-Haack reaction of acetanilides, (ii) oxidation of the corresponding alcohols. Vilsmeier-Haack reaction2-Chloroquinoline-3-carbaldehydes 2 were synthesized from acetanilides 1 via a VilsmeierHaack reaction either by traditional methods [14][15][16][17][18][19][20][21][22][23] or by microwave, 24 or ultrasonic irradiation (Scheme 1). 25Scheme 1 Reviews and Accounts ARKIVOC 2012 (i) 211-276Page 213 © ARKAT-USA, Inc. Oxidation of the corresponding alcohols(2-Chloroquinolin-3-yl)methanol 3 was oxidized to aldehyde 2 using a combination of diethyl diazene-1,2-dicarboxylate (DEAD) and catalytic ZnBr 2 in refluxing toluene (Scheme 2). 26Scheme 2 3 Chemical Reactions Substitution reactionsTreatment of 2-chloroquinoline-3-carbaldehydes 2 with prenyl thiolate or prenyl alcoholate 4 in the presence of sodium hydroxide or potassium t-butoxide, furnished S/O-prenyl aldehydes 5 in 72-84% yield, respectively. S/O-prenyl aldehyde 5, underwent imino Diels-Alder reactions with various substituted anilines in the presence of InCl 3 in acetonitrile resulting in the formation mixture of cis and trans products 7 and 8 in 55-71% yields by intramolecular cycloaddition reaction of the imine 6 generated in situ in the one pot-reaction (Scheme 3). 14 Scheme 3Knoevenagel hetero Diels-Alder reaction of 5 (X = O) with N,N'-dimethylbarbituric acid in water was carried out in the presence of piperidine at room temperature. The intermediate Knoevenagel adduct 9 was not isolated and allowed to cyclise at room temperature after 3 h stirring gave the cis-fused pentacyclic pyrano [2,3-b]quinoline derivatives 10 with high yield (80%) and diastereoselectivity (> 99%) (Scheme 4). 27 Scheme 4Recently, tetrahydrocyclopenta[c]acri...

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“…Over the past decade, various organic reactions have been found to perform successfully synthesis in water of 2-amino-1,3,4-thiadiazoles [5], pyrimido [4,5-d]pyrimidine [6], pyrano [2,3-c]pyrazoles [7], substituted 3,4-dihydropyrimidin-2(1H)-ones [8], 2-amino-4-(5-hydroxy-3-methyl-1H-pyra¬zol-4-yl)-4H chromene-3carbonitrile derivatives [9], spiroindoline-pyranopyrazoles [10] 2-aminothiazoles [11] and benzoin condensation [12].Type of N-heterocyclic carbenes (NHCs) (Figure 1) has attracted considerable interest in recent years due to their ability to reverse aldehydes' normal mode of reactivity, rendering them nucleophilic at the carbonyl carbon. Especially stetter reaction has received significant interest in organocatalyzed reactions due to their special electronic characteristics [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%