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

Anhydrides Dicarboxylic Acids Lactams Naphthalenesulfonates

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
21 01 2022
Historique:
pubmed: 11 1 2022
medline: 29 1 2022
entrez: 10 1 2022
Statut: ppublish

Résumé

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

Identifiants

DOI: 10.1021/acs.joc.1c02456 PMID: 35000381
pubmed: 35000381
doi: 10.1021/acs.joc.1c02456
doi:

Substances chimiques

Anhydrides 0
Dicarboxylic Acids 0
Lactams 0
Naphthalenesulfonates 0
naphthosultone 83-31-8

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

1537-1540

Auteurs

Andrey Firsov (A)

Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.

Olga Bakulina (O)

Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.

Dmitry Dar'in (D)

Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
ORCID: 0000-0002-0413-7413

Viktor V Sokolov (VV)

Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.

Mikhail Krasavin (M)

Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
ORCID: 0000-0002-0200-4772

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Anhydrides › Synthesis of γ-Sultam-Annelated δ-Lactams via...
questionsmedicales.fr › Composés chimiques organiques › Acides carboxyliques › Acides acycliques › Diacides carboxyliques › Synthesis of γ-Sultam-Annelated δ-Lactams via...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Lactames › Synthesis of γ-Sultam-Annelated δ-Lactams via...
questionsmedicales.fr › Composés polycycliques › Hydrocarbures aromatiques polycycliques › Naphtalènes › Naphtalènesulfonates › Synthesis of γ-Sultam-Annelated δ-Lactams via...