ArticleThe Journal of organic chemistry2019
A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.
Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed.
- Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.RSC advances · 2025Review
- Formaldehyde surrogates in multicomponent reactions.Beilstein journal of organic chemistry · 2025Review
- Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications.International journal of molecular sciences · 2023Review
- Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry.Topics in current chemistry (Cham) · 2022Review
- Direct oxidation ofRSC advances · 2021Article
- HCl•DMPU-Assisted One-pot and Metal-free Conversion of Aldehydes to Nitriles.Green chemistry : an international journal and green chemistry resource : GC · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
Abstract
We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yields with high functional group tolerance and scalability.
Identifiers
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.