Synthesis and Application of Heterocyclic Germatranes via Rhodium‐Catalyzed Directed C−H Activation/Annulation with Alkynyl Germatranes and Palladium‐Catalyzed Cross‐Coupling

Xu, Mengyu; Wang, Chao; Jiang, Weitao; Xiao, Bin

doi:10.1002/adsc.201901633

Cited by 18 publications

(9 citation statements)

References 76 publications

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“…The current system achieves various advantages like promptly accessible beginning materials, short response time, great yields, virtue of items, cost-viability, utilization of modest quantity of reasonable impetus and naturally harmless green dissolvable. High capability and simple operation make this new eco-accommodating procedure alluring for theoretical examination and planned applications [65].…”

Section: Scheme23: N-arylpyrrolederivatives Synthesis By Onepottwocom...mentioning

confidence: 99%

review on green multicomponent synthesis of heterocyclic compounds

D’souza

D’Souza

Mendonca

et al. 2022

ijhs

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Heterocyclic compounds are of very much concern in our daily life. These compounds constitute the largest and most varied family of organic compounds. Heterocyclic compounds have one or more hetero atoms in their structure., Day by day the number is increasing rapidly due to the enormous synthetic research and also their synthetic utility. They may be cyclic or non-cyclic in nature. They are predominantly used as pharmaceuticals, as agrochemicals and as veterinary products. They also find applications as sanitizers, developers, antioxidants, as corrosion inhibitors, as copolymers, dye stuff and anticancer drugs. They are used as vehicles in the synthesis of other organic compounds. In this review, we cover most biological active heterocyclic compounds that it’s recently synthesized or extracted from the plants e.g. antibiotics such as penicillin’s, cephalosporin; alkaloids such as vinblastine, morphine, reserpine etc. have heterocyclic moiety.

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Section: Scheme23: N-arylpyrrolederivatives Synthesis By Onepottwocom...mentioning

confidence: 99%

review on green multicomponent synthesis of heterocyclic compounds

D’souza

D’Souza

Mendonca

et al. 2022

ijhs

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“…Recently, Xiao (2020) introduced alkynyl germatranes to the Rh-catalyzed annulation strategy to synthesize a series of germanium-substituted heterocyclic compounds (Scheme 6). 12 The alkynyl germanium reagents were prepared from the corresponding alkynyl Grignard reagents or parent terminal alkynes in one-pot procedures. The masked germatrane group was inert under the standard cross-coupling conditions, whereas the annulated products could be coupled with haloarenes under TBAF (tetrabutylammonium fluoride)-promoted Pd-catalyzed conditions.…”

Section: Terminal Alkynesmentioning

confidence: 99%

Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems

2020

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Transition-metal-catalyzed C–H activation followed by oxidative cyclization with unsaturated coupling partners has been a valuable synthetic tool for the multiring molecular scaffolds. This Perspective introduces the recent progress on the Cp*M-catalyzed (M = Co, Rh, and Ir) oxidative direct annulation of functionalized arenes with terminal alkynes and their equivalents through C–H bond cleavage. The highlighted examples are categorized according to the 10 different types of reagents used in the transformations. The representative conditions, selected examples of the reaction scope, and key mechanistic aspects are briefly summarized.

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“…In this regard, 6-bromo isoquinolone is a pivotal substrate for the introduction of arene moieties at C-6, which can be readily achieved via metal-catalyzed arylation. 20 It is interesting to mention that the substitution of the 6-methoxy ether group in naturally occurring alkaloids such as doryphornine by ether-tethered azacyclic equivalents led to inhibitors of Rho kinase. 21 Increasing the sp 3 character of bioactive compounds often comprising stereogenic carbon atoms has proven beneficial for both their physical 22 and chemical properties.…”

Section: Introductionmentioning

confidence: 99%

“…Direct introduction of substituents at C-6 and C-7 in isoquinolones is scarce and requires prefunctionalization. In this regard, 6-bromo isoquinolone is a pivotal substrate for the introduction of arene moieties at C-6, which can be readily achieved via metal-catalyzed arylation . It is interesting to mention that the substitution of the 6-methoxy ether group in naturally occurring alkaloids such as doryphornine by ether-tethered azacyclic equivalents led to inhibitors of Rho kinase .…”

Section: Introductionmentioning

confidence: 99%

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

et al. 2020

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Naturally occurring isoquinolones have gained considerable attention over the years for their bioactive properties. While the late-stage introduction of various functionalities at certain positions, namely, C-3, C-4, and C-8, has been widely documented, the straightforward introduction of challenging sp 3 carbon-linked acyclic aminoalkyl or aza- and oxacyclic appendages at C-6 and C-7 remains largely underexplored. Interest in 6-substituted azacyclic analogues has recently garnered attention in connection with derivatives exhibiting anticancer activity. Reported here is the first application of the versatile and recently emerging field of Ni-catalyzed reductive cross-coupling reactions to the synthesis of 6- and 7- hetero(cyclo)alkyl-substituted isoquinolones. In a second and complementary approach, a new set of C-6- and C-7-substituted positional isomers of hetero(cyclo)alkyl appendages were obtained from the merging of photocatalytic and Ni-catalyzed coupling reactions. In both cases, 6- and 7-bromo isoquinolones served as dual-purpose reacting partners with readily available tosylates and carboxylic acids, respectively.

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Synthesis and Application of Heterocyclic Germatranes via Rhodium‐Catalyzed Directed C−H Activation/Annulation with Alkynyl Germatranes and Palladium‐Catalyzed Cross‐Coupling

Cited by 18 publications

References 76 publications

review on green multicomponent synthesis of heterocyclic compounds

review on green multicomponent synthesis of heterocyclic compounds

Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

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Synthesis and Application of Heterocyclic Germatranes via Rhodium‐Catalyzed Directed C−H Activation/Annulation with Alkynyl Germatranes and Palladium‐Catalyzed Cross‐Coupling

Cited by 18 publications

References 76 publications

review on green multicomponent synthesis of heterocyclic compounds

review on green multicomponent synthesis of heterocyclic compounds

Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp3/sp2-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

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Product

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About

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues