Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli-Cushman Reaction of Sultam-Based Dicarboxylic Acids

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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.

In: Journal of Organic Chemistry, Vol. 87, No. 2, 21.01.2022, p. 1537–1540.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{04d294cab5364147bb61ba1ac59ab2e3,

title = "Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli-Cushman Reaction of Sultam-Based Dicarboxylic Acids",

abstract = "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. ",

keywords = "DIASTEREOSELECTIVE SYNTHESIS, IMINES, DIVERSITY",

author = "Andrey Firsov and Olga Bakulina and Dmitry Dar'In and Sokolov, {Viktor V.} and Mikhail Krasavin",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = jan,

day = "21",

doi = "10.1021/acs.joc.1c02456",

language = "English",

volume = "87",

pages = "1537–1540",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

RIS

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

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