α-Lithiation of 1-Aryl-3,3-dialkyltriazenes and Intramolecular Conversion to Benzylamine and Tetrahydrobenzotriazine Derivatives

Nishiwaki, Koichi; Ogawa, Takashi; Matsuo, Keizo

doi:10.1002/1521-3757(20020201)114:3<502::aid-ange502>3.0.co;2-9

Cited by 6 publications

(1 citation statement)

References 45 publications

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“…The mentioned anionic cyclisation was applied to the amide intermediates 187 and 188 producing the corresponding tricyclic lactams, which are key compounds in the preparation of kanoid analogues [118]. Dearomatising intramolecular nucleophilic attack of carbanions 189 gave access to the benzylamine derivatives 190, after loss of nitrogen with restoration of the aromatic ring (Scheme 46) [119].…”

Section: Addition To Carbon-carbon Double Bondsmentioning

confidence: 99%

Non-Deprotonating Methodologies for Organolithium Reagents Starting from Non-Halogenated Materials. Part 2: Transmetallation and Addition to Multiple Bonds

Guijarro¹,

Pastor²,

Yus

2011

COC

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The recent publications on the topic of the preparation of organolithium reagents by non-deprotonating methodologies and starting from non-halogenated substrates have been covered in the present revision. In this second part, transmetallation processes, mainly tin-lithium exchange, and addition to multiple bonds have been considered. Moreover, other procedures, such as carbon-carbon bond scission and the Shapiro reaction, have been included.

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Section: Addition To Carbon-carbon Double Bondsmentioning

confidence: 99%

Non-Deprotonating Methodologies for Organolithium Reagents Starting from Non-Halogenated Materials. Part 2: Transmetallation and Addition to Multiple Bonds

Guijarro¹,

Pastor²,

Yus

2011

COC

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Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Suleymanov

Severin

2020

Angewandte Chemie

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Aromatic compounds containing triazenyl groups (N3RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has changed over the last five years, and it has become apparent that vinyl and alkynyl triazenes are highly interesting compounds with a unique reactivity. The electron‐donating properties of the triazenyl group provide alkynyl triazenes with an ynamide‐like reactivity, which can be exploited in reactions of the triple bond. Vinyl triazenes, on the other hand, can be used for electrophilic vinylation reactions. The foundation for this new triazene chemistry are synthetic pathways which allow preparing vinyl and alkynyl triazenes in few steps from readily available starting materials. In this Minireview, we summarize recent developments in this area.

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