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Synthesis of cyclopentane annulated δ‐lactams via diazomethane‐mediated CC bond cleavage of α‐keto N,O ‐hemiaminals

Year: 2024

Type: article

Abstract: Diazomethane‐mediated C‐C bond cleavage of α‐keto N,O‐hemiaminals was investigated for the first time. Diazomethane as a reagent result C‐C bond cleavage of norbornyl α‐keto N,O‐hemiaminals, Grob‐like fragmentation, lead to the formation of cyclopentane annulated δ‐lactams in excellent yields. We have synthesized the precursor norbornyl α‐keto N,O‐hemiaminal by the nucleophilic displacement of halogen of norbornyl α‐diketone with the various amines.

Source: Journal of Heterocyclic Chemistry

DOI: 10.1002/jhet.4829

Authors: Hari Mangeswara Rao Gorle, Satwinder Singh Marok

Institutions: Texila American University, Indian Institute of Technology Kanpur, Apotex (Canada)

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funder: Department of Science and Technology, Ministry of Science and Technology, India

OpenAlex ID: W4396808149

FWCI:

Cites: 37

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Related to: 10