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Hydrogenolysis of the CO bond of the 1,2,4‐oxadiazine ring. Adams platinum hydrogenation of 3‐aryl‐5,6‐dihydro‐5‐(substituted)‐methylene‐4 H ‐1,2,4‐oxadiazine derivatives
Author(s) -
Kawashima Etsuko,
Takada Toyozo,
Tabei Katsumi,
Kato Tetsuzo
Publication year - 1985
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.5570220557
Subject(s) - chemistry , hydrogenolysis , aryl , methylene , platinum , derivative (finance) , benzamide , stereochemistry , medicinal chemistry , ring (chemistry) , organic chemistry , catalysis , alkyl , financial economics , economics
Adams platinum hydrogenation of Z ‐3‐aryl‐5,6‐dihydro‐5‐(substituted)methylene‐4 H ‐1,2,4‐ oxadiazine ( 1a‐f ) proceeds very slowly through CO bond fission to give N ‐(1‐substitutedcarbonyl‐2‐propylidene)benzamide ox‐ime derivative 2 as the main product. In the reaction of 5‐(arylcarbamoyl)methylene analogues 1d‐f , 5‐(aryl‐carbamoyl)methyl‐5,6‐dihydro‐3‐phenyl‐4 H ‐1,2,4‐oxadiazine ( 4 ) and N ‐aryl‐3‐hydroxybutanamide derivative 5 are also obtained as well as compound 2 .