One-pot synthesis of <i>N</i>-substituted benzannulated triazoles <i>via</i> stable arene diazonium salts

McGrory, Rochelle; Faggyas, Réka J.; Sutherland, Andrew

doi:10.1039/d1ob00968k

Cited by 6 publications

(7 citation statements)

References 51 publications

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“…Additional references cited within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36]…”

Section: Methodsmentioning

confidence: 99%

Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst

Constantinou,

Gkizis,

Lagopanagiotopoulou

et al. 2023

Chemistry A European J

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The niche field of photochemistry offers opportunities that are not found in “traditional” ground state chemical pathways. Aminochlorinated derivatives are an interesting family of 1,2‐difunctionalised compounds that provide access to a variety of natural products and pharmaceutical active substances. A practical, catalyst‐free chloroamination protocol is described herein, providing access to intermediates of great importance, utilising mild and photochemical reaction conditions (370 nm), where N‐chlorosulfonamides are used as both nitrogen and chlorine sources. A wide variety of olefins, decorated with a plethora of functional groups, was tested providing excellent results (28 examples, 18–88 % yield). Mechanistic studies (UV‐Vis, control experiments and quantum yield measurement) were also performed.

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“…Additional references cited within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36]…”

Section: Methodsmentioning

confidence: 99%

Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst

Constantinou,

Gkizis,

Lagopanagiotopoulou

et al. 2023

Chemistry A European J

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“…The only red flag is the use of DCM as cosolvent; however, this can be replaced by a mixture of acetonitrile/water albeit at lower concentration. In contrast to this, previously reported protocols − for generating benzotriazin-4(3 H )-ones use potentially explosive diazonium salts, toxic reagents, harsh conditions, and/or large amounts of additives.…”

mentioning

confidence: 96%

“…The most common approach for preparing benzotriazin-4(3 H )-ones exploits the diazotization of 2-aminobenzamide or methyl anthranilate; however, the associated use of strong acids and NaNO 2 renders this method problematic and limits its scope (Scheme a). , Therefore, alternative routes to these attractive scaffolds have been developed in recent years. Modifications include a mild protocol using a polymer-supported nitrite reagent and p -tosic acid . Further variations were presented by Liu and collaborators using nitromethane or tert -butylnitrite as the nitrogen source and avoid the harsh acidic conditions required for diazonium salt formation reactions.…”

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confidence: 99%

Continuous Flow Synthesis of Benzotriazin-4(3H)-ones via Visible Light Mediated Nitrogen-Centered Norrish Reaction

García-Lacuna,

Baumann

2024

Org. Lett.

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We report a new protocol for the synthesis of substituted benzotriazin-4(3H)-ones which are underrepresented heterocyclic scaffolds with important pharmacological properties. Our method exploits acyclic aryl triazine precursors that undergo a photocyclization reaction upon exposure to violet light (420 nm). Continuous flow reactor technology is exploited to afford excellent yields in only 10 min residence time with no additives or photocatalysts needed. The underlying reaction mechanism appears to be based on an unprecedented variation of the classical Norrish type II reaction with concomitant fragmentation and formation of N−N bonds. Scalability, process robustness, and green credentials of this intriguing transformation are highlighted.

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“…The possibility of neighboring group participation was tested using aryl amines with methyl ketone and hydroxyl moieties; however, neighboring group participation was not observed in the case of 3zo and 3zp . The utilization of 2-aminobenzamides in the current diazotization and azo coupling conditions induced intramolecular diazo cyclization, , leading to 1,2,3-benzotrizine-4(3 H )-ones 5a–5c in 68–82% yields along with products 3zq–3zs in 5–7% yields.…”

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confidence: 99%

Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling

Ramesh

Kim

2023

Org. Lett.

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Secondary nitroalkanes underwent oxygen-mediated nitro−nitrite isomerization, serving as versatile N-nitrosating agents under aerobic conditions. To capitalize on the newly discovered aerobic nitro−nitrite isomerization phenomenon, a phase-transfer catalysis system employing KSeCN and TBAI was developed, in which the tandem diazotization and azo coupling with nitroalkanes as well as N-nitrosation of amines were accomplished. The current tandem diazotization and azo coupling strategy provides a facile synthesis of areneazo-2-(2-nitro)propane derivatives, a safe synthetic alternative to aryl diazonium salts.

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One-pot synthesis of N-substituted benzannulated triazoles via stable arene diazonium salts

Abstract: A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts,...

Cited by 6 publications

References 51 publications

Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst

Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst

Continuous Flow Synthesis of Benzotriazin-4(3H)-ones via Visible Light Mediated Nitrogen-Centered Norrish Reaction

Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling

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