The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli-Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center.

Nazar Moshnenko, Alexander Kazantsev, Olga Bakulina, Dmitry Dar'in, Mikhail Krasavin

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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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

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3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

The Castagnoli-Cushman Reaction.Molecules (Basel, Switzerland) · 2023
Review

4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Nazar MoshnenkoInstitute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.

Alexander KazantsevInstitute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.ORCID 0000-0002-0050-7288

Olga BakulinaInstitute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.

Dmitry Dar'inInstitute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.ORCID 0000-0002-0413-7413

Mikhail KrasavinInstitute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.ORCID 0000-0002-0200-4772

Funding

Government of Russian Federation 075- 15-2021-637Russian Foundation for Basic Research 20-03-00922

6 · The paper itself

Abstract

Novel aryl-substituted homophthalic acids were cyclodehydrated to the respective homophthalic anhydrides for use in the Castagnoli-Cushman reaction. With a range of imines, this reaction proceeded smoothly and delivered hitherto undescribed 4-aryl-substituted tetrahydroisoquinolonic acids with remarkable diastereoselectivity, good yields and no need for chromatographic purification. These findings significantly extend the range of cyclic anhydrides employable in the Castagnoli-Cushman reaction and signify access to a novel substitution pattern around the medicinally relevant tetrahydroisoquinolonic acid scaffold.

Indexed as

AnhydridesCarboxylic AcidsCarbonIminesMolecular StructureAnhydridesCarbonCarboxylic AcidsIminesall-carbon quaternary atomCastagnoli–Cushman reactionhomophthalic anhydrideiminelactamtetrahydroisoquinolone

Identifiers

PMID36500582

DOI10.3390/molecules27238462

PMCPMC9738897

What OpenQuestion holds

Textmetadata

LicenceCC BY

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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.