Evidence map›Paper›PMID 32281795›Full record

ArticleThe Journal of organic chemistry2020

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.

Angela S Carlson, En-Chih Liu, Joseph J Topczewski

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

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.

2 · The registry

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.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

2 citing papers in PubMed.

  1. Azides in the Synthesis of Various Heterocycles.Molecules (Basel, Switzerland) · 2022
    Review
  2. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

3 authors.

Angela S CarlsonDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.ORCID 0000-0002-6812-4662
En-Chih LiuDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
Joseph J TopczewskiDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.ORCID 0000-0002-9921-5102

Funding

Chiral α,α-Disubstituted Amine Synthesis by Dynamic Kinetic ResolutionR35GM124718 · NIGMS · UNIVERSITY OF MINNESOTA · PI TOPCZEWSKI, JOSEPH JOHN · 2017 to 2020
$1.5M
Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical ResearchS10OD011952 · OD · UNIVERSITY OF MINNESOTA · PI HOYE, THOMAS R. · 2012 to 2012
$378k
NIGMS NIH HHS R35 GM124718NIH HHS S10 OD011952
6 · The paper itself

Abstract

Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon atoms attached to a nitrogen atom. Over 30 examples are provided with an average isolated yield of 71% (ranging from 40% to 94%). The reaction was easily scaled to use more than one gram of starting material, and the products can be readily diversified.

Indexed as

AcrylatesAzidesMolecular StructurePyrazolesAcrylatesAzidesPyrazoles

Identifiers

PMID32281795
PMCPMC7294854

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Registered trials

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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.