Preparation of 3-Substituted Isoindolin-1-one, Cinnoline<u>,</u> and 1,2,4-[<i>e</i>]-Benzotriazine Derivatives

Dhaibi, Fatat B. El; Youssef, Ali; Fettinger, James C.; Kurth, Mark J.; Haddadin, Makhluf J.

doi:10.1021/acsomega.2c03045

Cited by 3 publications

(2 citation statements)

References 19 publications

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“…Some representative examples in this regard are shown in Figure . In addition, they have also found wide applications in the development of novel photoelectric materials, fluorescent brighteners, and dyes. , Meanwhile, the pyrazolidinone skeleton is prevalent in anti-inflammatory, analgesic, antipyretic, and anticonvulsant drugs (Figure ). Considering the importance of benzotriazine and pyrazolidinone, it is reasonable to infer that a hybrid skeleton combining these two privileged structural scaffolds might be bestowed with synergistic biological activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Pyrazolidinone-Fused Benzotriazines through C–H/N–H Bond Functionalization of 1-Phenylpyrazolidinones with Oxadiazolones

et al. 2023

J. Org. Chem.

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Presented herein is an efficient synthesis of pyrazolidinone-fused benzotriazines through the cascade reaction of 1-phenylpyrazolidinones with oxadiazolones. The formation of the title products is initiated by Rh(III)-catalyzed C–H/N–H bond metallation of 1-phenylpyrazolidinone and subsequent coordination with oxadiazolone followed by migratory insertion along with CO2 liberation, proto-demetallation, and intramolecular condensation. To our knowledge, this is the first synthesis of pyrazolidinone-fused benzotriazines based on the C–H bond activation strategy by using oxadiazolone as an easy-to-handle amidine surrogate. In general, this new protocol has advantages such as valuable products, easily accessible substrates, redox neutral conditions, concise synthetic procedure, high efficiency, and compatibility with diverse functional groups. Moreover, the usefulness of this method is further showcased by scale-up synthetic scenario and suitability to substrates derived from natural products such as thymol and nerol.

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Section: Introductionmentioning

confidence: 99%

“…Benzotriazine derivatives possess a broad spectrum of pharmaceutical properties . Some representative examples in this regard are shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazolidinone-Fused Benzotriazines through C–H/N–H Bond Functionalization of 1-Phenylpyrazolidinones with Oxadiazolones

et al. 2023

J. Org. Chem.

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A Novel Synthesis of Substituted Benzo[1,2,4]triazine Derivatives via Copper-Catalyzed Intermolecular N-Arylation of 2-Iodoaniline and Hydrazonoyl Chlorides

Nematpour,

Nouri

2024

Synlett

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In this contribution, a speedy and direct approach for the synthesis of benzo[1,2,4]triazine derivatives via a copper-catalyzed intermolecular N-arylation of 2-iodoaniline and hydrazonoyl chlorides is described. The reaction proceeds in THF at room temperature with no need for any ligand. The use of simple and readily available starting materials, mild copper-catalytic reaction conditions, and good yields (72–92%) are remarkable specifications of this protocol.

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Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines

Elkamhawy,

Jaragh-Alhadad,

Mekheimer

et al. 2023

Green Processing and Synthesis

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The synthesis of cinnolines has found great interest due to their diverse biological and industrial potency. Yet, the reported synthetic protocols for their synthesis showed limitations that involve harsh reaction conditions such as strong acidic or basic medium, low reaction yields, and using expensive and high loading catalysts. The C–H functionalization has been recognized as intriguing synthetic approach for the synthesis of aromatic/heteroaromatic scaffolds over the past two decades. Here, we reported a novel metal-catalyzed free photocatalytic synthesis of polyfunctionally substituted cinnolines. When ethyl 1-aryl-5-cyano-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylates and nitrostyrene derivatives are irradiated with white light (LED 30 W) in ethanol in the presence of piperidine (30 mol%) in open air for 8 h at room temperature, the corresponding polyfunctionally substituted cinnolines are obtained in excellent yields (90–95%) via C–H activation of pyridazine methyl group and nitrostyrene (–N═O) function. Several merits were achieved, which are as follows: (1) the reaction is metal-free; (2) the reaction proceeds with increasing energy efficiency; (3) diversity of functionally substituted cinnolines; (4) high EcoScale value, which reflects the greens of the reaction; and (5) ease handling either in conducting the reaction or in the isolation of products.

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Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives

Cited by 3 publications

References 19 publications

Synthesis of Pyrazolidinone-Fused Benzotriazines through C–H/N–H Bond Functionalization of 1-Phenylpyrazolidinones with Oxadiazolones

Synthesis of Pyrazolidinone-Fused Benzotriazines through C–H/N–H Bond Functionalization of 1-Phenylpyrazolidinones with Oxadiazolones

A Novel Synthesis of Substituted Benzo[1,2,4]triazine Derivatives via Copper-Catalyzed Intermolecular N-Arylation of 2-Iodoaniline and Hydrazonoyl Chlorides

Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines

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