An efficient synthesis of diimidazo[1,2-a:1′,2′-c]quinazolines via a copper-catalyzed double Ullmann cross-coupling reaction

The Carbon-Nitrogen bond formation has always been an important and useful tool in drug discovery. Its wide applications in synthesizing N-heterocycles, known as the most prevalent moiety in the active pharmacophores, have attracted increasing attention from researchers. In recent years many works were devoted to finding new and more rapid and effective chemo-and regio-selective methods for the synthesis of N-containing heterocycles. Buchwald-Hartwig and Ullman-Goldberg are two proven efficient methods for synthesizing five, six, and seven-membered heterocycles found abundantly in literature. Here, we study these two amination methods more precisely, based on the reaction conditions and the products.

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“…In some cases, 2-chloro-1H-benzo[d]imidazole derivatives 171 were used in the place of 2-bromo-1H-imidazol 169. [114]…”

Section: Six-membered Ring Formationmentioning

confidence: 99%

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

et al. 2021

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“…According to Wang et al, diimidazo[1,2-a:1',2'-c]quinazolines can be efficiently synthesized through a copper-catalyzed double Ullmann cross-coupling reaction between 2-(2-bromophenyl)-4,5-diphenyl-1H-imidazole and 2-bromo-1H-imidazole (Scheme 19). [37] In a one-pot process, this double Ullmann crosscoupling reaction constructed two new C(sp 2 )-N bonds and fused a tetracyclic heterocycle with four nitrogen atoms. Surprisingly, 2-bromobenzene rings with electron-withdrawing groups (À Cl or -F) and electron-donating groups (À Me or -OMe) reacted seamlessly with 2-bromo-1H-imidazole under the optimised reaction condition to produce the desired diimidazo[1,2-a:1',2'-c]quinazolines in appreciable yields.…”

Section: Transition Metal-catalyzed Cross Coupling Approachmentioning

confidence: 99%

An Extensive Analysis of Current Synthetic Methodologies and Applications of Imidazo/Benzimidazo[1,2‐c]Quinazolines

Bairy,

Sinha

2024

ChemistrySelect

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A great deal of attention has been received on developing N‐heterocyclic compounds due to their ambitious biological activities. Many of them are essential footstep to the development and discovery of new drugs. Imidazole/benzimidazole and quinazoline are essential pharmacologically active N‐heterocycles, and one of the molecular framework built up from their combination, imidazo/benzimidazo[1,2‐c]quinazoline, is of great attention in terms of synthesis, reactions, and medicinal applications. The positional variation of hetero N‐atoms and the functional groups acting as substituents in the main scaffold have a direct impact on the properties of imidazo/benzimidazo[1,2‐c]quinazolines. In addition to its physiological activities, this moiety is useful for electrical conductivity, molecules/ions sensing, coordination complex and coordination polymer (CP) formation, and their diverse applications. The major objective of this review is to highlight various synthetic approaches for imidazo/benzimidazo[1,2‐c]quinazolines motif since 2000. Toxicant‐free reaction conditions and the use of an extensive range of inexpensive substrates are two of the main practical benefits of the protocol in accomplishing the sustainable development goals.

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“…The reaction occurs via copper catalysis; two-fold N -arylation occurs simultaneously to form the corresponding tetracyclic imidazoquinazoline derivatives (Scheme 76). 95…”

Section: Tandem Copper-catalyzed N-arylation–c/n/o/s–arylationmentioning

confidence: 99%

“…Synthesis of diimidazo[1,2-a:10,20-c]quinazolinesLiu, Wang and co-workers developed a method in which the reaction between 2-(2-bromophenyl)-4,5-diphenyl-1H-imidazole and 2-bromoimidazole forms diimidazo[1,2-a:10,20-c] quinazolines. The reaction occurs via copper catalysis; two-fold N-arylation occurs simultaneously to form the corresponding tetracyclic imidazoquinazoline derivatives (Scheme 76) 95.…”

mentioning

confidence: 99%

Recent advances in the tandem copper-catalyzed Ullmann–GoldbergN-arylation–cyclization strategies

2022

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An efficient synthesis of diimidazo[1,2-a:1′,2′-c]quinazolines via a copper-catalyzed double Ullmann cross-coupling reaction

Cited by 8 publications

References 24 publications

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

An Extensive Analysis of Current Synthetic Methodologies and Applications of Imidazo/Benzimidazo[1,2‐c]Quinazolines

Recent advances in the tandem copper-catalyzed Ullmann–GoldbergN-arylation–cyclization strategies

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