Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli-Cushman Reaction of Sultam-Based Dicarboxylic Acids. / Firsov, Andrey; Bakulina, Olga; Dar'In, Dmitry; Sokolov, Viktor V.; Krasavin, Mikhail.
в: Journal of Organic Chemistry, Том 87, № 2, 21.01.2022, стр. 1537–1540.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli-Cushman Reaction of Sultam-Based Dicarboxylic Acids
AU - Firsov, Andrey
AU - Bakulina, Olga
AU - Dar'In, Dmitry
AU - Sokolov, Viktor V.
AU - Krasavin, Mikhail
N1 - Publisher Copyright: © 2022 American Chemical Society.
PY - 2022/1/21
Y1 - 2022/1/21
N2 - An unusual type of highly reactive sultam-based dicarboxylic acids and correscponding anhydrides was employed in the Castagnoli-Cushman reaction delivering diastereomerically pure adducts at room temperature. Due to steric congestion, the initial adducts were prone to decarboxylation affording diastereomeric mixtures of bicyclic sultam lactams, separable by HPLC. The choice of a protecting group on the sultam nitrogen atom allows liberation of the NH-sultam, which is not only suitable for further modification but represents a known pharmacophore for carbonic anhydrase inhibition.
AB - An unusual type of highly reactive sultam-based dicarboxylic acids and correscponding anhydrides was employed in the Castagnoli-Cushman reaction delivering diastereomerically pure adducts at room temperature. Due to steric congestion, the initial adducts were prone to decarboxylation affording diastereomeric mixtures of bicyclic sultam lactams, separable by HPLC. The choice of a protecting group on the sultam nitrogen atom allows liberation of the NH-sultam, which is not only suitable for further modification but represents a known pharmacophore for carbonic anhydrase inhibition.
KW - DIASTEREOSELECTIVE SYNTHESIS
KW - IMINES
KW - DIVERSITY
UR - http://www.scopus.com/inward/record.url?scp=85123284606&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/67ea45d6-e2c9-318e-b8bc-9b8756a158b7/
U2 - 10.1021/acs.joc.1c02456
DO - 10.1021/acs.joc.1c02456
M3 - Article
AN - SCOPUS:85123284606
VL - 87
SP - 1537
EP - 1540
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -
ID: 92206253