Chemistry of sulfonylmethyl isocyanides.  11.  Synthesis of 1,2,4-triazoles from tosylmethyl isocyanide and aryldiazonium compounds

Leusen, A. M. Van; Hoogenboom, Bernard E.; Houwing, H.

doi:10.1021/jo00866a031

Cited by 31 publications

(11 citation statements)

References 6 publications

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“…Leusen and co‐workers developed an analogous base‐promoted addition and cyclization strategy based on tosylmethyl isocyanide 92 and electron‐rich aryl diazonium salts (Scheme 24b), giving rise to 1,3‐disubstituted 1,2,4‐triazoles 93 in conjunction with the formation of 1,5‐disubstituted counterparts 94 as minor products. [ 152 ]…”

Section: Cyclization and Cycloaddition Reactions For The Constructionmentioning

confidence: 99%

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

et al. 2020

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Aryl diazonium salts occupy a privileged role in synthetic chemistry owing to their ready availability and versatile reactivity. While their applications in accessing diversely functionalized arene derivatives via denitrogenation‐coupling and reduction/addition reactions have been well recognized by practitioners in both academia and industry, recent renaissance in chemical transformations of retaining the key N2‐unit has emerged as a powerful technique to construct various N‐heterocycles. This review covers the history and latest advances in cyclization and cycloaddition reactions using aryl diazonium salts as N2‐annulation synthons. The scope, applications, and opportunities in exploring new chemical space by this sustainable strategy are summarized and discussed.

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Section: Cyclization and Cycloaddition Reactions For The Constructionmentioning

confidence: 99%

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

et al. 2020

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“…Synthesized compounds were well characterized by spectroscopic analysis and melting point of all compounds were also corrected. [25]…”

Section: Synthesis Of Triazole Scaffoldmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

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p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

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“…The later compounds are of interest and pharmacological importance due to their potential applications as anticonvulsant, anti-inflammatory, 9 antitumor, 10 and antimycobacterial 11 agents, they have also been shown to inhibit b-fibril formation. 12 The present methodology provides selectively 2-imino-3aminobenzofurans 5a-f from a 2-hydroxybenzaldehyde (2), an amine 3, and p-toluenesulfonylmethyl isocyanide (4, Scheme 1), in a one-pot process under mild reaction conditions in 39-71% yield, 13 adding a new derivative to the list of the formidable van Leusen reaction which provides a broad diversity of heterocycles, such as oxazoles, 14 imidazoles, 14,15 indoles, 16 triazoles, 17 and pyrroles. 18 The 1 H NMR and 13 C NMR spectra evidenced the formation of the new heterocycle; selected spectroscopic data 1.…”

Section: Figurementioning

confidence: 99%

Synthesis of 2-Imino-3-aminobenzofurans via Multicomponent Reactions from TosMIC

García‐González¹,

González‐Zamora²,

Santillán³

et al. 2011

Synlett

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Chemistry of sulfonylmethyl isocyanides. 11. Synthesis of 1,2,4-triazoles from tosylmethyl isocyanide and aryldiazonium compounds

Cited by 31 publications

References 6 publications

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Synthesis of 2-Imino-3-aminobenzofurans via Multicomponent Reactions from TosMIC

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