Evidence map›Paper›PMID 31807201›Full record

ArticleBeilstein journal of organic chemistry2019

Unexpected one-pot formation of the 1

Sergey A Dobrynin, Igor A Kirilyuk, Yuri V Gatilov, Andrey A Kuzhelev, Olesya A Krumkacheva, Matvey V Fedin, Michael K Bowman, Elena G Bagryanskaya

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Beilstein journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it
0cells of the map it votes in
0citing 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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

8 authors.

Sergey A DobryninN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0003-3486-0335
Igor A KirilyukN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0001-6033-0368
Yuri V GatilovN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0002-4128-7293
Andrey A KuzhelevN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0003-3445-2921
Olesya A KrumkachevaNovosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russia.
Matvey V FedinNovosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russia.
Michael K BowmanN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0003-3464-9409
Elena G BagryanskayaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia.ORCID https://orcid.org/0000-0003-0057-383X

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The unexpected formation of a highly strained polycyclic amine was observed in a one-pot synthesis from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction includes 1,3-dipolar cycloaddition of dimethyl fumarate to the cyclic azomethine ylide formed in situ from cyclopentanone and ammonia. The polycyclic amine product was easily converted into a sterically shielded polycyclic nitroxide. The EPR spectra and spin relaxation behavior of the nitroxide were studied in solution. The spin relaxation seems well suited for the use as a biological spin label and are comparable with those of cyclic nitroxides with two spirocyclic moieties adjacent to the N-O

Indexed as

domino reactionsEPRnitroxidespin relaxation

Identifiers

PMID31807201
PMCPMC6880831

What OpenQuestion holds

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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.