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Reductive Transformations of 6 H ‐1,2‐Oxazines with Hydride Reagents: Formation of Aziridines and 3‐Hydroxyalkylated 1,2‐oxazines
Author(s) -
Zimmer Reinhold,
Homann Kai,
Reißig HansUlrich
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301186
Subject(s) - oxazines , chemistry , substituent , alkoxy group , reagent , hydride , tributyltin hydride , medicinal chemistry , ketone , organic chemistry , combinatorial chemistry , hydrogen , alkyl
6 H ‐1,2‐Oxazines 1 and 3 are converted into aziridines 2 and 4 , respectively, by reduction with LiAlH 4 . Reduction of 1,2‐oxazine 5 lacking the 6‐alkoxy substituent leads to phenyl ketone 6 , 6‐Alkoxy‐substituted 1,2‐oxazine‐3‐carboxylates 7 , 9 , and 11 are reduced with NaBH 4 to give the corresponding 3‐hydroxymethylated compounds 8 , 10 , and 12 in good yields.