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Polycyclic azetidines. I. The preparation of benzo [ c ]‐ cis ‐6‐azabicyclo[3.2.0] heptane
Author(s) -
Murray Robert J.,
Cromwell Norman H.
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110623
Subject(s) - chemistry , heptane , oxime , azetidine , indene , adduct , hydroxymethyl , organic chemistry , medicinal chemistry , stereochemistry
The title compound was prepared from compounds readily obtained from 2‐carbomethoxy‐I‐indanone oxime ( 5 ) or from the N ‐chlorosulfonyl isocyanate adduct of indene ( 9 ). Apart from its ability to undergo transformation to the azetidine, compound 9 upon refluxing with excess LAII was found to undergo reductive decompostion to cis ‐2‐hydroxymethyl‐1‐indanamine ( 2 ).
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