Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles

Jiang, Nan; Ren, Xin; Qiang, Yan; Liu, Shilei; Wang, Jing; Ma, Yangmin; Szostak, Michal

doi:10.1039/d3sc00301a

Cited by 5 publications

(3 citation statements)

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“…operation at 24 h (Table 1, entry 19). We also investigated a set of representative solvents, and DMF was proven to be the best choice for this synthetic methodology (Table 1, entries [20][21][22][23]. Furthermore, Pd-catalysts were explored as a catalyst system, but the desired product was hardly observed (Table 1, entries 24-25).…”

Section: Resultsmentioning

confidence: 99%

“…Among these creative approaches, the transition-metalcatalyzed C-H activation strategy of indoles has taken a prominent role. Generally, the activation of the C-H bond of alkylenes requires the participation of transition-metal catalysts [12][13][14][15][16][17] and the assistance of directing groups (amide [18][19][20][21], pyridyl [22,23], pyrimidyl [24], imidazole [25], carboxylic ester [26], and methoxy [27]). In particular, Stuart reported the first example of the synthesis of indoles from N-phenyl-2-aminopyridine and alkyne or alkene via intramolecular oxidative C-N coupling and C-H activation by [Cp*RhCl 2 ] 2 [28].…”

Section: Introductionmentioning

confidence: 99%

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Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

et al. 2023

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1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a moderate to good yield, and all of the N-(2-triazine) indoles were characterized by 1H NMR, 13C NMR, and HRMS. This protocol can apply to the gram-scale synthesis of the N-(2-triazine) indole in a moderate yield. Moreover, the reaction is proposed to be performed via a six-membered ruthenacycle (II) intermediate, which suggests that the triazine ring could offer chelation assistance for the formation of N-(2-triazine) indoles.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

et al. 2023

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“…11a It is remarkable that more readily available and cheaper anilines as the raw materials for the construction of benzoxazoles have scarcely been explored. 12 Moreover, developing efficient methods for the synthesis of benzoxazoles is highly important. N,N-Dimethylformamide (DMF) has been widely used as a polar solvent in various reactions due to its relative stability, low cost, and ready availability.…”

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confidence: 99%

Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis

Long

Wang

et al. 2023

J. Org. Chem.

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Herein, we disclose a practical and simple procedure to synthesize 2-aminobenzoxaoles. Simple anilines and formamides were used as substrates. The C−H bond ortho to the amino group in the anilines was directly functionalized under cobalt-catalyzed conditions with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a Lewis acid for this reaction. The mechanism study showed that this transformation may involve a radical process.

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Hypervalent Iodine Mediated Synthesis of 2‐Aminobenzazoles and 2‐Aminobenzothiazoles

Gu,

Li,

et al. 2024

Asian J Org Chem

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The hypervalent iodine mediated, silica gel promoted synthesis of 2‐aminobenzazoles and 2‐aminobenzothiazole derivatives under metal‐free mild conditions within short time (30min) has been developed. Under this process, PhI(COOCF3)2 (PIFA) or PhI(COOCH3)2 (PIDA) acts as an oxidant and radical initiator direct activated the ortho‐C‐H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and suitable for practical application.

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Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles

Abstract: Direct functionalization of the C(O)–N amide bond is one of the most high-profile research directions in the last decades, however oxidative couplings involving amide bonds and functionalization of thioamide C(S)–N...

Cited by 5 publications

References 96 publications

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis

Hypervalent Iodine Mediated Synthesis of 2‐Aminobenzazoles and 2‐Aminobenzothiazoles

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