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Synthesis of aminomethylazetidines regioselective reactions of mesyloxymethylazetidinones with nucleophiles II
Author(s) -
Boros Éva,
Bertha Ferenc,
Czira Gábor,
Feller Antal,
Fetter József,
KajtárPeredy Mária,
Simig Gyula
Publication year - 2006
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.5570430218
Subject(s) - chemistry , regioselectivity , azetidine , lithium aluminium hydride , nucleophile , lithium (medication) , ring (chemistry) , nucleophilic substitution , aluminum hydride , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , methoxide , endocrinology
Two efficient methods have been developed for the synthesis of variously substituted 2‐aminomethylazetidine derivatives 5 by regioselective nucleophilic substitution of 4‐mesyloxymethylazetidin‐2‐ones 3 followed by reduction or by reduction of the appropriate 4‐oxo‐azetidine‐2‐carboxamides 7 . A novel ring transformation of 4‐oxoazetidine‐2‐carboxamides 7 into tetrahydroquinolines 16 by reaction with lithium aluminium hydride/aluminium trichloride has been investigated.