ArticleNature communications2018
Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 52 citations in OpenAlex.
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- Discovery, synthesis, and cytotoxic evaluation of isoquinolinequinones produced byRSC advances · 2023Article
- Modular and practical diamination of allenes.Nature communications · 2023Article
- Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes.Nature communications · 2022Article
- Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdAngewandte Chemie (International ed. in English) · 2022Article
- Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.The Journal of organic chemistry · 2022Article
- Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.Nature communications · 2020Article
- A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.The Journal of organic chemistry · 2019Article
- Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles.Nature communications · 2018Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 2 countries.
Funding
Abstract
Saturated 1,4-diazo heterocycles including piperazines, 1,4-diazepanes, and 1,4-diazocanes, are highly important for therapeutic development, but their syntheses are often tedious. We describe here an amphoteric diamination strategy to unite readily available 1,2-, 1,3- or 1,4-diamine derivatives with electron-deficient allenes via a formal [n + 2] (n = 4, 5, 6) cyclization mode to produce the corresponding 1,4-diazo heterocycles in just one step. This strategy features mild reaction conditions, high functional group tolerance, and scalability (gram scale). The reagents used are cheap and readily available and no transition metal catalysts are needed. More sophisticated products containing trifluoromethyl group or bicyclic ring systems can be accessed via a one-pot procedure as well. Our mechanistic studies support that formation of mono-iodinated or chlorinated diamine intermediates is important for the desired transformation and the commonly proposed chloride-iodide exchange process and a radical N-C bond formation is unlikely when the combination of NCS/KI is used.
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