A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles.

Angela S Carlson, Alexandru M Petre, Joseph J Topczewski

Abstract read

In one paragraph

Article in Tetrahedron letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing 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

1 citing paper in PubMed.

A Review of the Recent Development in the Synthesis and Biological Evaluations of Pyrazole Derivatives.Biomedicines · 2022
Review

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, MN 55455, United States.

Alexandru M PetreDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, MN 55455, United States.

Joseph J TopczewskiDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, MN 55455, United States.

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

This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%-72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

Indexed as

AzideCascade reactionPyrazolePyrrolidineVinyl sulfone

Identifiers

PMID34054152

DOI10.1016/j.tetlet.2021.152860

PMCPMC8153508

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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.