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@article{042eafa105ad44fd9bc99584776734f6,
title = "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",
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.",
keywords = "all-carbon quaternary atom, Castagnoli–Cushman reaction, homophthalic anhydride, imine, lactam, tetrahydroisoquinolone",
author = "Nazar Moshnenko and Alexander Kazantsev and Olga Bakulina and Dmitry Dar{\textquoteright}in and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2022 by the authors.",
year = "2022",
month = dec,
doi = "10.3390/molecules27238462",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "MDPI AG",
number = "23",

}

RIS

TY - JOUR

T1 - 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

AU - Moshnenko, Nazar

AU - Kazantsev, Alexander

AU - Bakulina, Olga

AU - Dar’in, Dmitry

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2022 by the authors.

PY - 2022/12

Y1 - 2022/12

N2 - 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.

AB - 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.

KW - all-carbon quaternary atom

KW - Castagnoli–Cushman reaction

KW - homophthalic anhydride

KW - imine

KW - lactam

KW - tetrahydroisoquinolone

UR - http://www.scopus.com/inward/record.url?scp=85143636278&partnerID=8YFLogxK

U2 - 10.3390/molecules27238462

DO - 10.3390/molecules27238462

M3 - Article

C2 - 36500582

AN - SCOPUS:85143636278

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 23

M1 - 8462

ER -

ID: 101522560