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A Novel Class of 7-Membered Heterocyclic Compounds.

ABSTRACT: The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on ?-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the ?-position is fully retained.

SUBMITTER: Bauer A

PROVIDER: S-EPMC7496137 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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A Novel Class of 7-Membered Heterocyclic Compounds.

Bauer Adriano A Borsos Eszter E Maulide Nuno N

European journal of organic chemistry 20200506 26

The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully ...[more]

PMID: 32982576

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