Carbonylation Chemistry Applied to the Synthesis of Benzimidazo[2,1‐<i>b</i>]quinazolin‐12‐ones

Vangrunderbeeck, Sarah; Balcaen, Tim; Veryser, Cedrick; Steurs, Gert; Borggraeve, Wim M. De

doi:10.1002/ejoc.202101136

Cited by 3 publications

(7 citation statements)

References 36 publications

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“…[4,5]imidazo[2,1-b]quinazolin-12(6H)-one (2m). 7 White solid (0.0841 g, 80% yield); mp 300−302 °C; R f 0.29 (40% EtOAc/hexanes); 1 H NMR [500 MHz, CDCl 3 + TFA (2 drops)]: δ 8.47 (dd, J = 8.0, 1.5 Hz, 1H), 8.38 (s, 1H), 7.94 (ddd, J = 8.0, 7.2, 1.5 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.60 (ddd, J = 8.0, 7.2, 1.5 Hz, 1H), 7.55 (s, 1H), 2.47 (s, 3H), 2.44 (s, 3H); 13 C{ 1 H} NMR [125 MHz, CDCl 3 + TFA (2 drops)]: δ 156.8, 143.7, 138.3, 137.1, 137.0, 135. 3,128.5,126.7,126.4,123.9,118.0,116.5,114.5,113.7,20.6,20.4.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…(2c). 7 White solid (0.0744 g, 75% yield); mp 363−365 °C; R f 0.36 (40% EtOAc/hexanes); 1 H NMR [500 MHz, CDCl 3 + TFA (2 drops)]: δ 8.63 (d, J = 8.5 Hz, 1H), 8.25 (s, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.75 (dd, J = 8.0, 2.0 Hz, 1H), 7.64 (t, J = 8.5 Hz, 1H), 7.63 (d, J = 8.5 Hz, 1H), 7.56 (t, J = 8.5 Hz, 1H), 2.56 (s, 3H); 13 C{ 1 H} NMR [125 MHz, CDCl 3 + TFA (2 drops)]: δ 156. 8, 144.4, 138.4, 136.9, 135.1, 128.9, 128.3, 127.8, 125.8, 125.4, 118.1, 116.4, 114.5, 113.5, 21.7. 2-Bromobenzo [4,5]imidazo [2,1-b]quinazolin-12(6H)-one (2d).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…13a White solid (0.0816 g, 76% yield); mp 342−344 °C; R f 0.33 (40% EtOAc/hexanes); 1 H NMR [500 MHz, CDCl 3 + TFA (2 drops)]: δ 8.54 (d, J = 8. 5 Hz,1H),8.46 (dd,J = 8.0,1.5 Hz,1H),7.93 (ddd,J = 8.5,7.2, 2.0 Hz, 1H), 7.76 (d, J = 2.0 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.58 (ddd, J = 8.0, 7.1, 1.0 Hz, 1H), 7.51 (dd, J = 8.5, 2.0 Hz, 1H); 13 C{ 1 H} NMR [125 MHz, CDCl 3 + TFA (2 drops)]: δ 156. 6,145.8,137.7,136.9,134.0,130.6,128.4,126.2,125.5,124.5,118.6,117.1,114.6,quinazoline-2,4(1H,3H)-dione (4).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Considering their potential benefits, several synthetic methods have been developed to prepare linearly and angularly fused benzimidazoquinazolinones as shown in Scheme . A wide range of starting materials have been used to prepare the linear benzimidazoquinazolinones including N -(2-bromophenyl)-1 H -benzimidazol-2-amines, (2-aminophenyl)(1 H -azol-1-yl)methanone, 2-aminobenzoyl chlorides and N -alkyl substituted benzimidazoles, N -anilinoquinazolinones, 2-azido- N -(2-bromophenyl)benzamides, substituted 2-bromo- N -(2-halophenyl)benzamides, as well as o -aryl isothiocyanate esters (Scheme a). Alternative synthetic routes have also been developed for the synthesis of angularly fused benzimidazoquinazolinones that employ cyclization reactions of 2-substituted benzimidazole derivatives such as 2-(2-aminophenyl)benzimidazole, 2-(2-azidophenyl)benzimidazole, 2-(2-nitrophenyl)-benzimidazoles, and 2-(2-bromoarylbenzimidazoles) .…”

Section: Introductionmentioning

confidence: 99%

“…1 H NMR [500 MHz, CDCl 3 + TFA (2 drops)]: δ 8.54 (d, J = 8.0 Hz, 1H), 8.39 (d, J = 8.0 Hz, 1H), 7.87 (t, J = 8.0 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H), 7.59−7.48 (m, 3H); 13 C{ 1 H} NMR [125 MHz, CDCl 3 + TFA (2 drops)]: δ 156.8, 144.2, 137.3, 137.0, 128.6, 128.5, 126.7, 125.8, 125.7, 118.1, 116.4, 114.6, 113.5.2-Methylbenzo[4,5]imidazo[2,1-b]quinazolin-12(6H)-one (2c) 7. White solid (0.0744 g, 75% yield); mp 363−365 °C; R f 0.36 (40% EtOAc/hexanes); 1 H NMR [500 MHz, CDCl 3 + TFA (2 drops)]: δ 8.63 (d, J = 8.5 Hz, 1H), 8.25 (s, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.75 (dd, J = 8.0, 2.0 Hz, 1H), 7.64 (t, J = 8.5 Hz, 1H), 7.63 (d, J = 8.5 Hz, 1H), 7.56 (t, J = 8.5 Hz, 1H), 2.56 (s, 3H); 13 C{ 1 H} NMR [125 MHz, CDCl 3 + TFA (2 drops)]: δ 156.8, 144.4, 138.4, 136.9, 135.1, 128.9, 128.3, 127.8, 125.8, 125.4, 118.1, 116.4, 114.5, 113.5, 21.7.…”

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confidence: 99%

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Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides

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Ph3P–I2-mediated condensation reactions of isatoic anhydrides and o-phenylenediamines have been developed for the regioselective syntheses of a wide range of linearly and angularly fused benzoimidazoquinazolinones. The selectivity of the products relies on the generation of either highly electrophilic oxyphosphonium or less reactive imidate intermediates. A direct amine attack at the C-2 position of the oxyphosphonium intermediate presumably drives the reaction toward the linearly fused products, whereas an attack of the diamine at the C-4 position of the in situ generated cyclic imidate leads to the angularly fused derivatives. This strategy serves as a practical handle for the efficient synthesis of other related heterocycles.

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Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides

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Synthesis, characterization, in vitro antimycobacterial and cytotoxicity evaluation, DFT calculations, molecular docking and ADME studies of new isomeric benzimidazole-1,2,3-triazole-quinoline hybrid mixtures

Nyoni,

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et al. 2023

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Synthesis of N-Alkyl Substituted Benzimidazoquinazolinones

Dake,

Blanchard,

Kaliappan

2024

ACS Omega

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Aromatic N-heterocycles, especially benzimidazoquinazolinones featuring alkyl chains, hold significant pharmaceutical relevance. Here, we introduce a streamlined one-pot, 2-fold Cu-catalyzed C−N bond formation protocol for the efficient synthesis of diverse N-alkyl benzimidazoquinazolinone derivatives. This method showcases a broad substrate scope, leveraging readily accessible alkyl halides and delivers the desired cyclized products in excellent yields. Additionally, the methodology enabled the synthesis of an antitumor agent with satisfactory yield, highlighting its utility in medicinal chemistry endeavors.

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Carbonylation Chemistry Applied to the Synthesis of Benzimidazo[2,1‐b]quinazolin‐12‐ones

Cited by 3 publications

References 36 publications

Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides

Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides

Synthesis, characterization, in vitro antimycobacterial and cytotoxicity evaluation, DFT calculations, molecular docking and ADME studies of new isomeric benzimidazole-1,2,3-triazole-quinoline hybrid mixtures

Synthesis of N-Alkyl Substituted Benzimidazoquinazolinones

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