Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of <i>N</i>-arylpyrazoles

Liu, Jidan; Xu, Er-Jie; Jiang, Jinyuan; Zeng, Huang; Zheng, Liyao; Liu, Zhao‐Qing

doi:10.1039/c9cc09657d

Cited by 58 publications

(19 citation statements)

References 61 publications

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“…In 2020, Liu and co‐workers reported a novel and efficient strategy for the synthesis of structurally diverse N ‐arylpyrazoles through copper‐mediated tandem ring‐opening/cyclization reactions of cyclopropanols with aryldiazonium salts (Scheme 11). [21] This transformation was initiated with the generation of β ‐keto alkyl radical intermediates via Cu(OAc) 2 ‐mediated oxidative radical ring‐opening of cyclopropanols, followed by radical addition to aryldiazonium salts and annulations. The reaction enabled the formation of two C−N bonds in a single reaction and featured a simple operation, excellent regioselectivity, and a good tolerance of a broad range of functional groups to afford the desired N ‐arylpyrazole derivatives in good to excellent yields.…”

Section: Synthesis Of Pyrazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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Nitrogen heterocycles are important structural subunits that occur widely in bioactive natural products, pharmaceuticals, agrochemicals, dyes, cosmetics, and functional materials. Considering the importance of these useful compounds in modern science, the synthesis of N-heterocycles and their derivatives has always been a hot topic in organic synthesis. Recently, arenediazonium salts which can be easily prepared from inexpensive and abundantly available anilines, have been used as versatile nitrogen sources in the field of nitrogen heterocycle synthetic chemistry due to their ready availability, rich reactivity, and diverse transformations. The aim of the present review is to summarize the recent advances in the synthesis of nitrogen heterocycles using arenediazonium salts as nitrogen sources in the past ten years. Hopefully, it can provide practical guidance for the readers who are interested in utilizing arenediazonium salts as building blocks in organic synthesis. For simplicity and clarity, the organization of this review is based on the number of N atoms in the ring of nitrogen heterocycle.

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Section: Synthesis Of Pyrazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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“…Our study found that the levels of adrenaline, norepinephrine, aldosterone and cortisol in the observation group were lower than those in the control group (P<0.05), indicating the post-traumatic stress response in the observation group was low (35). Compared with the control group, the protein expression of IL-6, IL-17 and CRP in the observation group were decreased (P<0.05) (36).…”

Section: Gene Expression Resultsmentioning

confidence: 53%

Study of ultrasound-guided ropivacaine combined with butorphanol continuous paravertebral block to prevent pain syndrome by evaluating ccl2 gene expression after radical mastectomy

Xiaochen

Cui²,

Shan³

et al. 2022

Cell Mol Biol (Noisy-le-grand)

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This study aimed to investigate the clinical effect of ultrasound-guided ropivacaine combined with butorphanol continuous paravertebral block in preventing postoperative pain syndrome of breast cancer. For this purpose, 100 women treated for breast cancer from April 2018 to July 2019 were enrolled as research objects. Surgical procedures included local sentinel lymph node biopsy, mastectomy, sentinel lymph node biopsy for mastectomy, modified radical mastectomy, and implantation. The selected patients were randomly divided into two groups: control group (routine operation anesthesia; n = 50) and observation group (ultrasound-guided thoracic paravertebral block before induction of ropivacaine+butorphanol anesthesia; n = 50). The Real-time PCR technique was performed to evaluate CCL2 gene expression. VAS scores were recorded during the postoperative period. Compared with the control group, the observation group had lower VAS scores at six h, 24h, and 48h (P<0.05). The pain effect of the observation group was less than that of the control group. The observation group had better analgesic effects after anesthesia. The observation group had a lower incidence of pain syndrome at the 6th, 8th, and 12th months (P<0.05), and the incidence of pain syndrome in the two groups decreased with the extension of time. The observation group had lower levels of related factors (P<0.05), and the observation group had lower traumatic stress responses. The protein expression of IL-6, IL-17, and CRP in the observation group was lower than that in the control group (P<0.05). The results of CCL2 gene expression also showed that gene expression in the control group increased significantly (P=0.0047). Since the expression of this gene is one of the factors that stimulate pain signals in the body, the method used in the present study was able to reduce the amount of pain significantly. Therefore, the combination of ropivacaine combined with butorphanol ultrasound-assisted paravertebral block can reduce the intensity of postoperative pain in patients with breast cancer surgery, decrease the incidence of pain syndrome, and increase pain tolerance.

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“…Very recently, the potential of using aryl diazonium salts to access pyrazoles was further highlighted by Liu and co‐workers (Scheme 23). [ 132 ] They took advantage of cyclopropanols 86 to proceed ring‐opening and then cyclize with aryl diazonium salts 30 to generate N ‐arylpyrazoles 87 with excellent regioselectivity. Although stoichiometric copper salt was unavoidable for achieving good conversions, a major spotlight is that this reaction could accomplish in only 5 min at room temperature.…”

Section: Cyclization and Cycloaddition Reactions For The Constructionmentioning

confidence: 99%

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

et al. 2020

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Aryl diazonium salts occupy a privileged role in synthetic chemistry owing to their ready availability and versatile reactivity. While their applications in accessing diversely functionalized arene derivatives via denitrogenation‐coupling and reduction/addition reactions have been well recognized by practitioners in both academia and industry, recent renaissance in chemical transformations of retaining the key N2‐unit has emerged as a powerful technique to construct various N‐heterocycles. This review covers the history and latest advances in cyclization and cycloaddition reactions using aryl diazonium salts as N2‐annulation synthons. The scope, applications, and opportunities in exploring new chemical space by this sustainable strategy are summarized and discussed.

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Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles

Abstract: A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed.

Cited by 58 publications

References 61 publications

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Study of ultrasound-guided ropivacaine combined with butorphanol continuous paravertebral block to prevent pain syndrome by evaluating ccl2 gene expression after radical mastectomy

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

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