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p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates.

ABSTRACT: The amidine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene) display nucleophilic behaviour towards highly electrophilic p-nitrophenyl carbonate derivatives with ring opening of the bicyclic ring to form corresponding substituted ?-caprolactam and ?-lactam derived carbamates. This simple method presents a unified strategy to synthesize structurally diverse ?-caprolactam and ?-lactam compounds with a large substrate scope.

SUBMITTER: Vangala M

PROVIDER: S-EPMC5082618 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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<i>p</i>-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates.

Vangala Madhuri M Shinde Ganesh P GP

Beilstein journal of organic chemistry 20160926

The amidine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene) display nucleophilic behaviour towards highly electrophilic <i>p</i>-nitrophenyl carbonate derivatives with ring opening of the bicyclic ring to form corresponding substituted ε-caprolactam and γ-lactam derived carbamates. This simple method presents a unified strategy to synthesize structurally diverse ε-caprolactam and γ-lactam compounds with a large substrate scope. ...[more]

PMID: 27829914

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