4.8 Article

Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing an ortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines

Journal

ORGANIC LETTERS
Volume 17, Issue 21, Pages 5180-5183

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02484

Keywords

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Funding

  1. National Nature Science Foundation of China [20972051, 21476078, 08431901800, 08430703900]

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A novel one-pot efficient synthesis of 2,5-dihydro-1H-benzo[c]azepines and 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines from alpha-amino acids and aromatic aldehydes containing an ortho-Michael acceptor is reported via decarboxylative annulations without metal catalysts in yields of 52-91%. Under microwave irradiation, this protocol provides rapid access to polycyclic ring systems (only 5 min in most cases).

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