Convenient synthesis of some 2‐substituted 4(3<i>H</i>)‐quinazolinone derivatives

Philipova, Irena; Dobrikov, Georgi M.; Krumova, Katerina; Kaneti, José

doi:10.1002/jhet.5570430436

Cited by 19 publications

(19 citation statements)

References 28 publications

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“…Several methods have been developed to date for the synthesis of 2-styrylquinazolin-4(3 H )-ones and these include the reaction of anthranilic acid with styrylcarboxylic acids followed by amine insertion [1], and Knoevenagel condensation of 2-methyl-3-substituted quinazolin-4(3 H )-ones with aromatic aldehydes in the presence of a base or acid [7,15,16,17]. Amidation of 2-aminobenzonitrile with 3-arylacryloyl chlorides, followed by oxidative ring closure under basic conditions also afforded 2-styrylquinazolin-4(3 H )-ones [18].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

et al. 2015

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Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, d-f to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

et al. 2015

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“…A convenient synthesis of 2‐substituted 4(3 H )‐quinazolinonestyryl derivatives ( 140 ) was reported by Philipova et al. [59] (Scheme 33). The reaction of double lithiated 2‐methylquinazolin‐4(3 H )‐one ( 138 ) with a variety of aromatic aldehydes was described.…”

Section: Styryl Dyesmentioning

confidence: 99%

Styryl dyes – synthesis and applications during the last 15 years

Deligeorgiev

Vasilev

Kaloyanova

et al. 2010

Coloration Technology

101

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One of the most widely used and important groups of functional dyes are the styryl dyes and a review of this functional dye class has not been published for more than 15 years. In this review article, we describe the new trends in the synthesis of a range of novel intermediates and styryl dyes and include the most interesting examples of their high‐tech applications. However, this review is not intended to be comprehensive because of the large number of styryl dye studies that have been carried out in this time. Styryl cyanine dyes are widely used in optical recording media in laser discs, as flexible dyes, laser dyes, as optical sensitisers and in various other fields, for example dye‐sensitised solar cells and dyes with non‐linear optical properties. Additionally, the most important applications for these dyes are in bio‐labelling and in medicinal analysis.

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“…[143][144][145] Lithiation was regioselective at the carbon to the 2-position of the 3H-quinazolin-4-one moiety to give the dilithium reagents 222 (Scheme 28). [143][144][145] Reactions of 222 with various electrophiles gave the corresponding 2-substituted derivatives 223-252 (Scheme 28) in good yields (Tables 15 and 16). 143 Yield of isolated product after crystallization.…”

Section: Lateral Lithiation Of 2-n-alkyl-3h-quinazolin-4-onesmentioning

confidence: 99%

Reactions of organolithium reagents with quinazoline derivatives

El‐Hiti¹,

Hegazy²,

Alotaibi³

et al. 2012

Arkivoc

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This review deals with directed and regioselective lithiation of various quinazoline derivatives by the use of alkyllithiums in anhydrous THF at low temperature. Reactions of the lithium reagents obtained from the lithiation reactions with a range of electrophiles give the corresponding substituted derivatives in high yields. The procedures are simple, efficient and general to provide derivatives which might be difficult to produce by other means. In some cases nucleophilic addition of alkyllithiums takes place to produce the corresponding addition products via 1,2-and 3,4-additions. In other cases nucleophilic substitution or halogen-lithium exchange reactions occur.

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Convenient synthesis of some 2‐substituted 4(3H)‐quinazolinone derivatives

Cited by 19 publications

References 28 publications

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

Styryl dyes – synthesis and applications during the last 15 years

Reactions of organolithium reagents with quinazoline derivatives

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