Palladium-Catalyzed Intermolecular Aerobic Annulation of <i>o</i>-Alkenylanilines and Alkynes for Quinoline Synthesis

Zheng, Jia; Li, Zun; Huang, Liangbin; Wu, Wanqing; Li, Jianxiao; Jiang, Huanfeng

doi:10.1021/acs.orglett.6b01008

Cited by 61 publications

(23 citation statements)

References 56 publications

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“…Moreover, intermediate 52 could be isolated and characterized to provide the first mechanistic evidence of [2+2+2] cyclization reactions through a chloropalladation process. This reaction was not unique: in 2016, a palladium‐catalyzed aerobic [4+2] cyclization of o vinylaniline and alkynes was also developed by our group for quinoline synthesis with C−N and C−C bond formations and C−C bond cleavage (Scheme ) . It should be noted that O 2 acted as the oxidant, which also played an important role in cleavage of the C−C bond.…”

Section: O2 As the Co‐oxidantmentioning

confidence: 99%

“…This reactionw as not unique:i n 2016, ap alladium-catalyzed aerobic [4+ +2] cyclization of ovinylaniline and alkynes was also developed by our group for quinoline synthesis with CÀNa nd CÀCb ondf ormations and CÀCb ondc leavage( Scheme 36). [56] It should be noted that O 2 acted as the oxidant, which also played an important role in cleavage of the CÀCb ond.…”

Section: O 2 As the Co-oxidantmentioning

confidence: 99%

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Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Jiang

2019

ChemSusChem

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Transition‐metal‐catalyzed oxidative functionalization of alkenes has emerged as a powerful and valuable tool in modern organic synthesis. Recently, many methods have been established for the assembly of C−C and C–heteroatom bonds, which provides tremendous possibility for application in biology, medicine, and materials science. However, the use of stoichiometric amounts of strong oxidants leads to poor selectivity, low atom economy, and a series of undesired waste products. By contrast, green oxidants, such as O2, H2O2, or tert‐butyl hydroperoxide (TBHP), have bright prospects due to their attributes of mild, low cost, and great sustainability in transition‐metal‐catalyzed oxidation reactions. Based on the great and unique potential for the development of aerobic reactions, this review mainly highlights homogenous palladium‐catalyzed green oxidations of alkenes that have been reported in recent years. These methods provide new strategies for the transformation and functionalization of alkenes; some of them have also been successfully applied to the synthesis of the core structures of drugs and natural products. Additionally, through in‐depth studies of the reaction mechanisms in this field, it is believed that palladium‐catalyzed green oxidation reactions of alkenes with O2, H2O2, or TBHP will create added value for organic synthetic chemistry.

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Section: O2 As the Co‐oxidantmentioning

confidence: 99%

Section: O 2 As the Co-oxidantmentioning

confidence: 99%

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Jiang

2019

ChemSusChem

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“…Similarly, Zhou's group disclosed an efficient approach for the preparation of quinolines through a Pd II ‐catalyzed reaction of 2‐amino aromatic ketones and alkynes (Scheme b) . Recently, Jiang's group developed an efficient method for the synthesis of functionalized quinolines by using a C–C double bond cleavage reaction (Scheme c) . In addition, the synthesis of quinolines by Ru‐catalyzed cyclization processes has also been reported by the Kapur, Sun, and Hu groups, respectively.…”

Section: Introductionmentioning

confidence: 98%

Copper‐Catalyzed Tandem Reaction of Enamino Esters with ortho‐Halogenated Aromatic Carbonyls: One‐Pot Approach to Functionalized Quinolines

Peng

Liu

et al. 2018

Eur J Org Chem

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An efficient and practical approach for the synthesis of functionalized quinolines has been developed by using the copper‐catalyzed tandem C–C bond formation and C–N coupling reaction of enamino esters and ortho‐halogenated aromatic carbonyl compounds. Various functional groups were tolerated under the reaction conditions, and a series of quinolines were easily obtained in moderate to good yields. A gram‐scale reaction was also performed to demonstrate a further application of this synthetic method.

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“…14 This event was shown in Figure 1. 12,19 The easy synthesis of quinolines with selected chemical properties and their environmental sustainability [20][21][22] are added bonuses for their use in research and clinics, if proven to be effective anticancer drugs. Autophagy enables cellular adaptation to increased mutagenic load or to changes in nutrient concentrations.…”

Section: Introductionmentioning

confidence: 99%

Dissecting pharmacological effects of chloroquine in cancer treatment: interference with inflammatory signaling pathways

2019

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Chloroquines are 4-aminoquinoline-based drugs mainly used to treat malaria. At pharmacological concentrations, they have significant effects on tissue homeostasis, targeting diverse signaling pathways in mammalian cells. A key target pathway is autophagy, which regulates macromolecule turnover in the cell. In addition to affecting cellular metabolism and bioenergetic flow equilibrium, autophagy plays a pivotal role at the interface between inflammation and cancer progression. Chloroquines consequently have critical effects in tissue metabolic activity and importantly, in key functions of the immune system. In this article, we will review the work addressing the role of chloroquines in the homeostasis of mammalian tissue, and the potential strengths and weaknesses concerning their use in cancer therapy.

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Palladium-Catalyzed Intermolecular Aerobic Annulation of o-Alkenylanilines and Alkynes for Quinoline Synthesis

Cited by 61 publications

References 56 publications

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Copper‐Catalyzed Tandem Reaction of Enamino Esters with ortho‐Halogenated Aromatic Carbonyls: One‐Pot Approach to Functionalized Quinolines

Dissecting pharmacological effects of chloroquine in cancer treatment: interference with inflammatory signaling pathways

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