Synthesis of 2-Azaadamantan-6-one: A Missing Isomer | Zendy

Jianbo Wu | Zendy; Derek A. Leas | Zendy; Yuxiang Dong | Zendy; Xiaofang Wang | Zendy; Edward L. Ezell | Zendy; Douglas E. Stack | Zendy; Jonathan L. Vennerstrom | Zendy

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Synthesis of 2-Azaadamantan-6-one: A Missing Isomer

Author(s) -

Jianbo Wu,

Derek A. Leas,

Yuxiang Dong,

Xiaofang Wang,

Edward L. Ezell,

Douglas E. Stack,

Jonathan L. Vennerstrom

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b01819

Subject(s) - aziridine , curtius rearrangement , chemistry , bicyclic molecule , ring (chemistry) , epoxide , intramolecular force , carboxylic acid , ethylene , carbamate , stereochemistry , medicinal chemistry , intramolecular reaction , organic chemistry , catalysis

2-Azaadamantan-6-one and its Boc and ethylene ketal derivatives were synthesized from 9-oxo endo -bicyclo[3.3.1]non-6-ene-3-carboxylic acid. Similarly, the Cbz, Boc, and ethylene ketal derivatives of 2-azaadamantan-4-one were synthesized from endo -bicyclo[3.3.1]non-6-ene-3-carboxylic acid. Key steps were Curtius rearrangements to form benzyl carbamates, followed by spontaneous intramolecular attack of the carbamate nitrogen on transient bromonium ion or epoxide intermediates to effect ring closure to azaadamantane intermediates. The reaction sequence leading to 2-azaadamantan-6-one is consistent with the formation of a transient tetracyclic keto aziridine intermediate.

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