Synthesis of Benzo[<i>c</i>][2,7]naphthyridinones and Benzo[<i>c</i>][2,6]naphthyridinones via Ruthenium-Catalyzed [2+2+2] Cycloaddition between 1,7-Diynes and Cyanamides

Huvelle, Steve; Matton, Pascal; Tran, Christine; Rager, Marie‐Noëlle; Haddad, Mansour; Ratovelomanana‐Vidal, Virginie

doi:10.1021/acs.orglett.2c01963

Cited by 6 publications

(3 citation statements)

References 52 publications

(61 reference statements)

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“…In 2022, Vidal et al reported a Ru(II)-catalyzed synthesis of benzo [c][2,7] naphthyridinones (83) from 1,7-diynes (82) and cyanamides (81) via [2 + 2 + 2] cycloaddition (Scheme 34). [36] This method is applicable to both internal and terminal diynes and a variety of cyanamides with diverse functional group tolerance.…”

Section: Alkyne Insertion Via [2 + 2 + 2] Cycloadditionmentioning

confidence: 99%

The Renaissance of Organo Nitriles in Organic Synthesis

Rakshit

Dhara

Sahoo

et al. 2022

Chemistry An Asian Journal

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In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is of immense importance. The presence of nucleophilic N-atom, π-coordinating ability of the triple bond, and electrophilic C-center imparts unique and interesting reactivities. Owing to the ability of the nitrile to transform into various other functional groups or intermediates, the chemistry is very rich and diverse. In particular, the involvement of nitrile in numerous organic reactions such as inter-or intramolecular alkyne insertion, [2 + 2 + 2] cycloaddition with alkynes, [3 + 2] cycloaddition with azides, [4 + 2] cycloaddition with dienes allow the synthesis of many important carbo-and heterocycles. Furthermore, the nitrile serves as a directing group in many CÀ H bond functionalization reactions to introduce diverse functionalities and participate as a radical acceptor in radical cascade strategies to obtain a large variety of functional molecules. This review mainly focuses on the reactivity and diverse synthetic application of the nitrile including CÀ H bond functionalization, alkyne insertion, cycloaddition, and thermal or photochemical cascade strategy. The objective of the current review aims at bringing out the striking collection of various nitrile-triggered organic transformations.

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Section: Alkyne Insertion Via [2 + 2 + 2] Cycloadditionmentioning

confidence: 99%

The Renaissance of Organo Nitriles in Organic Synthesis

Rakshit

Dhara

Sahoo

et al. 2022

Chemistry An Asian Journal

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“…Over the years, the tandem annulation of 1, n -diynes has become an applicable and attractive tool for the collection of isocyclic and heterocyclic compounds via synergistic processes across its carbon–carbon triple-bond π system in an atom-economical manner ( Singidi et al, 2010 ; Wang et al, 2017 ; Chintawar et al, 2019 ). For instance, Vidal and colleagues established Ru-catalyzed [2+2+2] cycloaddition of amide-linked 1,7-diynes with electron-rich cyanamide for forming benzo[ c ][2,7]naphthyridinones as a major product in good yields and regioselectivities ( Scheme 1B ) ( Huvelle et al, 2022 ). Additionally, photocatalytic Kharasch-type-addition cyclization of 1, n -diynes provides another sustainable way of yielding various functionalized ring structures ( Wang et al, 2021 ; Wu et al, 2021 ; Zheng et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Photoinduced radical tandem annulation of 1,7-diynes: an approach for divergent assembly of functionalized quinolin-2(1H)-ones

Chen,

Song,

Yan

et al. 2024

Front. Chem.

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The first photocatalytic trichloromethyl radical-triggered annulative reactions of amide-linked 1,7-diynes with polyhalomethanes were established for the flexible assembly of functionalized quinolin-2(1H)-ones with generally acceptable yields. With the installation of the aryl group (R1) into the alkynyl moiety, C-center radical-initiated Kharasch-type addition/nucleophilic substitution/elimination cascade to produce quinolin-2(1H)-ones-incorporating gem-dihaloalkene, whereas three examples of polyhalogenated quinolin-2(1H)-ones were afforded when amide-linked 1,7-diynes bearing two terminal alkyne units were subjected to BrCX3 by exploiting dry acetonitrile as a solvent.

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“…Moreover, the cross-cyclization of 1,7-diynes with nitrile derivatives has already been proved to be a powerful strategy for the obtention of functionalized aminopyridine substrates. As a continuation of our investigations on transition metal-catalyzed cycloaddition, 18 we hypothesized that novel 5 H -chromeno[3,4- c ]pyridines could be obtained through ruthenium-catalyzed [2 + 2 + 2] cycloaddition reactions. To the best of our knowledge, such an approach has not been reported so far (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%