Lewis acid-catalyzed 2-arylquinazoline formation from N′-arylbenzimidamides and paraformaldehyde

Xiong, Cheng; Wang, Huamin; Xiao, Fuhong; Deng, Guo‐Jun

doi:10.1039/c6gc02319c

Cited by 44 publications

(20 citation statements)

References 54 publications

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“…Significantly, quinazolines are pharmaceutical molecules that can be modified to obtain other useful compounds. For example, 9a can be transferred to β‐glucuronidase inhibitor through a single step . To apply the GO‐catalyzed system to a wide scope, the dehydrogenations of 1,2,3,4‐tetrahydroquinoxaline (Table , E ) and 1,2,3,4‐tetrahydrobenzo[ b ]azepin‐5‐ones (Table , F ) were also tested.…”

Section: Methodsmentioning

confidence: 99%

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal‐Free Catalyst under Air

Zhang

Chen

et al. 2017

Adv Synth Catal

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Graphene oxide (GO) has been developed as an inexpensive,e nvironmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles.V aluable compounds,s uch as quinoline, 3,4-dihydroisoquinoline,q uinazoline,a nd indole derivatives,h aveb een successfully used as substrates.T he investigation of various oxygen-containing molecules with different conjugateds ystems indicated that botht he oxygen-containing groups and large p-conjugated system in GO sheets are essential for this reaction.

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Section: Methodsmentioning

confidence: 99%

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal‐Free Catalyst under Air

Zhang

Chen

et al. 2017

Adv Synth Catal

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“…Next, 3 [30f] is protonated to form a carbenium ion intermediate 4. [23] An electrophilic addition reaction between the carbenium ion and benzene ring then takes place to yield intermediate 5, which loses a proton to form dihydroquinazoline 6. [20] Finally, 6 is oxidized and aromatized by DMSO [30c] to generate the target product (1 aa).…”

Section: Resultsmentioning

confidence: 99%

“…Although quinazolines can be synthesized using the methods described above, these strategies require complex pre-functionalization of the substrate , [14,15,19] or the use of transition metal catalysts, [20,21,22] and excess oxidants. [23] Therefore, a facile, efficient, and more specific strategy for the synthesis of quinazolines is highly desirable. Herein, we report an N-arylamidine-based strategy using DMSO as a carbon source, which does not require the addition of acid, transition metal catalysis, or an external oxidant, for the efficient synthesis of quinazoline compounds.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Synthesis of 2‐Aryl Quinazolines via Tandem C−H/N−H Bond Functionalization

et al. 2021

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CÀ N bond formation is crucial for the preparation of synthetic organic nitrogen-containing heterocyclic compounds. This work provides a facile and highly efficient strategy (ca. ∼ 92 %) for the synthesis of quinazoline compounds, which involves tandem CÀ H/NÀ H bond functionalization using metal-free conditions without the need for an external oxidant. Mean-while, the reaction system exhibits good functional group tolerance and a wide substrate scope. Furthermore, our corresponding isotope tracking experiments have shown that dimethyl sulfoxide acts as a carbon source. Finally, this work affords a new strategy toward the further design and synthesis of heteroaromatic rings.

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“…To verify the synthetic utility of our method, the reaction of 1 a and 2 a was performed on 10 mmol scale. Product 3 aa was smoothly produced using a constant current (20 mA) in 82% yields (Scheme ), which is a proven useful β ‐glucuronidase inhibitor . Next, we successfully applied this method to the one‐pot synthesis of mackinazolinone 15 in 51% overall yield.…”

Section: Resultsmentioning

confidence: 99%

One‐Pot Synthesis of Quinazolin‐4(3H)‐ones through Anodic Oxidation and the Related Mechanistic Studies

et al. 2018

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A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib.

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Lewis acid-catalyzed 2-arylquinazoline formation from N′-arylbenzimidamides and paraformaldehyde

Abstract: An efficient procedure for the synthesis of 2-arylquinazolines from N′-arylbenzimidamides has been developed under transition-metal-free conditions.

Cited by 44 publications

References 54 publications

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal‐Free Catalyst under Air

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal‐Free Catalyst under Air

Metal‐Free Synthesis of 2‐Aryl Quinazolines via Tandem C−H/N−H Bond Functionalization

One‐Pot Synthesis of Quinazolin‐4(3H)‐ones through Anodic Oxidation and the Related Mechanistic Studies

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