Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals To Afford Bicyclic N-Heterocycles | Zendy

Yarkali Krishna | Zendy; Kola Shilpa | Zendy; Fujie Tanaka | Zendy

Open Access

Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals To Afford Bicyclic N-Heterocycles

Author(s) -

Yarkali Krishna,

Kola Shilpa,

Fujie Tanaka

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03210

Subject(s) - moiety , chemistry , intramolecular force , nucleophile , annulation , bicyclic molecule , electrophile , substituent , enol , mannich reaction , lactam , michael reaction , stereochemistry , medicinal chemistry , catalysis , organic chemistry

Acid-catalyzed intramolecular vinylogous Mannich reactions and intramolecular Michael reactions affording pyrrolizinone-fused N-heterocycles from hydroxylactam derivatives bearing enals have been developed. Depending on the substituent on the hydroxylactam, the enal moiety acted either as a nucleophile (i.e., as an enol/enolate) or as an electrophile to react with the N -acyliminium ion or enamide generated from the hydroxylactam moiety, respectively. The reactions were demonstrated in the construction of fused N-heterocycles with 5- to 8-membered rings.

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