Research output: Contribution to journal › Article › peer-review
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. / Moshnenko, Nazar; Kazantsev, Alexander; Bakulina, Olga; Dar’in, Dmitry; Krasavin, Mikhail.
In: Molecules, Vol. 27, No. 23, 8462, 12.2022.Research output: Contribution to journal › Article › peer-review
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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