Visible Light‐Induced Aerobic Oxidation of Indoles: One‐Pot Formation of 4‐Quinolones at Room Temperature

Ji, Xiaochen; Li, Dongdong; Wang, Zhongzhen; Tan, Muyun; Huang, Huawen; Deng, Guo‐Jun

doi:10.1002/ajoc.201800036

Cited by 28 publications

(11 citation statements)

References 90 publications

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“…The ene reaction of substrate 1 with 1 O 2 intially gives hydroperoxide 5, which under basic conditions undergoes rapid CÀC cleavage to keto amide 7 via the unstable 1,2dioxetane 6. The enolate 8 cyclizes by aldol condensation ("Camps" cyclization [17] ) to give 4-quinolone 2 as product of a photochemical Witkop-Winterfeldt [18] -type reaction. The singlet oxygenation of 2 followed by ring cleavage of a second dioxetane 9, via a charge-transfer-induced decomposition, [19] generates product 3.…”

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confidence: 99%

Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N‐Diacyliminium Ions

et al. 2020

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Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1,2‐a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N‐diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis.

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Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N‐Diacyliminium Ions

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“…[62] On the basis of the visible light-induced aerobic oxidative CÀ C bond cleavage of indoles, [149] Huang and coworkers reported one-pot synthesis of 4-quinolones starting from indoles (Scheme 70). [150] This cascade reaction involves a photocatalytic aerobic oxidation of indoles using visible light and the subsequent basepromoted Camps cyclization. The advantages of the present protocol include the use of environmentally benign and inexpensive oxygen as the sole oxidant, easy handling at room temperature, and step-economy.…”

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confidence: 99%

Aerobic Oxidative Functionalization of Indoles

et al. 2020

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The synthetic methodology for direct indole functionalizations is of great significance in indole chemistry and has been intensively investigated in the last few decades. From the perspective of green chemistry, oxygen is the best choice as the terminal oxidant in molecular synthesis. Hence, aerobic oxidative functionalization of indoles became a hot research topic in the last decade. Numerous efficient protocols in this field have been discovered that enable facile and efficient transformations of indoles to related valuable compounds, which are summarized and discussed in detail in this review.

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“…Reaction conditions were optimized for oxidant, solvent, and temperature conditions. The coupling of quinolone derivative (61) with ammonium thiocyanate (62) in the presence of K 2 S 2 O 8 (2 eqiv.) as an oxidant, DMSO as a solvent at room temperature for 17 h provided the best yield of 3-thiocyanoquinolones (63).…”

Section: Synthesis Of 4-quinolones Using An Organic/inorganic Catalystmentioning

confidence: 99%

“…N-free indole and N-Ts indole resulted in poor product yields. The mechanism was investigated and shown below infigure 17 [62]. Scheme 20.…”

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Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

2020

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The ubiquitous presence of 4-quinolones and its derivatives in a wide range of natural as well as synthetic drug molecules made them molecule of utmost importance for organic and medicinal chemists. Their wide array of biological activities such as antimicrobial, anticancer, anti-HIV, genitourinary infection, antifilarial, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Moreover, they are valuable intermediates for the synthesis of various fused heterocyclic compounds of synthetic and medicinal importance. Considering their array of synthetic and biological importance, new strategies for the synthesis of 4-quinolones and their derivatives have been designed and successfully demonstrated by researchers around the globe. The present review covers recent advances in the synthetic chemistry of 4quinolones since 2015 along with an insight into their mechanistic studies. We hope that the review article will serve as a valuable tool for the scientific community engaged in the synthesis and utilization of 4-quinolones and their derivatives.

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Visible Light‐Induced Aerobic Oxidation of Indoles: One‐Pot Formation of 4‐Quinolones at Room Temperature

Cited by 28 publications

References 90 publications

Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N‐Diacyliminium Ions

Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N‐Diacyliminium Ions

Aerobic Oxidative Functionalization of Indoles

Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

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