Convenient synthesis of 2-amino-3-(arylthio)indoles <i>via</i> the Rh-catalyzed reaction of 3-diazoindol-2-imines with thioesters

Ma, Fanghui; Qian, Jing; Lü, Ping; Wang, Yanguang

doi:10.1039/c7ob02597a

Cited by 19 publications

(12 citation statements)

References 45 publications

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“…3-Diazoindolin-2imines 21 with electron-withdrawing or electrondonating substituents on aromatic ring reacted smoothly to afford the corresponding products 50 in good yields (Scheme 16). [23] In 2019, Wang and colleagues developed a sequential process to access 5H-pyrazino [2,3-b]indoles starting from 3-diazoindolin-2-imines 21 (Scheme 17). The multi-step procedure started from a rhodiumcatalyzed NÀ H insertion reaction of Rh-carbene with enamines 51, affording products 52 in high yields.…”

Section: -Diazoindol-2-imines As Starting Materialsmentioning

confidence: 99%

“…3‐Diazoindolin‐2‐imines 21 with electron‐withdrawing or electron‐donating substituents on aromatic ring reacted smoothly to afford the corresponding products 50 in good yields (Scheme 16). [23] …”

Section: ‐Diazoindol‐2‐imines As Starting Materialsmentioning

confidence: 99%

“…[22] In 2018, Wang and co-workers reported a rhodiumcatalyzed [5 + 3] ). [23] In 2019, Wang and colleagues developed a sequential process to access 5H-pyrazino [2,3-b]indoles starting from 3-diazoindolin-2-imines 21 (Scheme 17). The multi-step procedure started from a rhodiumcatalyzed NÀ H insertion reaction of Rh-carbene with enamines 51, affording products 52 in high yields.…”

Section: -Diazoindol-2-imines As Starting Materialsmentioning

confidence: 99%

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Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Zhao

Gou

et al. 2021

Adv Synth Catal

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Indole-based heterocycles containing sulfur or nitrogen atoms are important frameworks that occur widely in biological active natural products and drugs. Consequently, several novel chemical transformations and new catalytic strategies have been developed for the preparation of these skeletons in a highly efficient and selective manner. This review focuses on recent advancements in the construction of indole-fused heterocyclic compounds by using iminoindolines, 3-diazoindol-2-imines, 2-thioxoindolines, and their derivatives as starting materials.

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Section: -Diazoindol-2-imines As Starting Materialsmentioning

confidence: 99%

Section: ‐Diazoindol‐2‐imines As Starting Materialsmentioning

confidence: 99%

Section: -Diazoindol-2-imines As Starting Materialsmentioning

confidence: 99%

See 1 more Smart Citation

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Zhao

Gou

et al. 2021

Adv Synth Catal

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“…[79] The substrate scope was broad with regard to both the starting materials and in this process a new C(sp ). [80] The products were obtained through a nucleophilic attack of sulfur atom onto Rh-carbene intermediate followed by 1,3migration of the acyl group. When, cyclic thioester 264 were examined under standard reaction conditions, 7,8-dihydrobenzo [7,8][1,4]thiazo-cino [3,2-b]indol-6(5H)-ones 266 were isolated in good yields.…”

Section: Insertion Reaction Of 3-diazoindolin-2-iminesmentioning

confidence: 99%

Catalytic Insertion Reactions of α‐Imino Carbenoids

Pal

Volla

2021

The Chemical Record

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Over the past decade, α-imino carbenoids generated via transition metal (such as rhodium, nickel, copper, palladium, silver) catalyzed denitrogenative ring-opening of N-sulfonyl-1,2,3-triazoles have found an extensive account of applications in synthetic organic chemistry. Particularly, they have been widely utilized as a donor/acceptor carbene complex in a range of transformations leading to diverse nitrogen containing compounds and heterocycles. Along the same direction, 3-diazoindolin-2-imines were successfully applied as an alternative source of αimino carbenoid precursors for the development of a number of methodologies to access diverse indole derivatives. This review summarizes the insertion reactions of α-imino metal carbenes derived from N-sulfonyl-1,2,3-triazoles and 3-diazoindolin-2-imines.

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“…1b ). Although Wang et al reported an aromatic indolyl C(sp 2 )–S bond formation from the reaction of 3-diazoindol-2-imines with thioesters 56 , the formation of vinyl C(sp 2 )–S bond via the sulfonium ylides rearrangement of the reaction of sulfur-containing compounds with diazo compounds is still unknown.…”

Section: Introductionmentioning

confidence: 99%

Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens

Liu

Tang

et al. 2021

Nat Commun

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Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds. Tetrasubstituted vinyl sulfides, which include both sulfur atom and tetrasubstituted alkenes motifs, might be a suitable skeleton for the discovery of the new material molecules and drug with unique functions and properties. However, how to modular synthesis these kinds of compounds is still challenging. Herein, a chemo- and stereo-selective Rh(II)-catalyzed [1,4]-acyl rearrangements of α-diazo carbonyl compounds and thioesters has been developed, providing a modular strategy to a library of 63 tetrasubstituted vinyl sulfides. In this transformation, the yield is up to 95% and the turnover number is up to 3650. The mechanism of this reaction is investigated by combining experiments and density functional theory calculation. Moreover, the “aggregation-induced emission” effect of tetrasubstituted vinyl sulfides were also investigated, which might useful in functional material, biological imaging and chemicalnsing via structural modification.

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Convenient synthesis of 2-amino-3-(arylthio)indoles via the Rh-catalyzed reaction of 3-diazoindol-2-imines with thioesters

Cited by 19 publications

References 45 publications

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Catalytic Insertion Reactions of α‐Imino Carbenoids

Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens

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