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Cycloaddition reaction of schiff bases with ketenes generated by pyrolysis of 2‐aryl‐substituted 1,5,7‐trioxaspiro[2.5]octane‐4,8‐diones
Author(s) -
Tsuno Takashi,
Kondo Kosuke,
Sugiyama Kunio
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.5570430104
Subject(s) - chemistry , octane , cycloaddition , aryl , lactam , medicinal chemistry , catalysis , pyrolysis , organic chemistry , bicyclic molecule , alkyl
The α‐oxo ketenes 6 which are generated by the pyrolysis of the 2‐aryl‐substituted 1,5,7‐trioxaspiro[2.5]octane‐4,8‐diones 1 , were reacted with Schiff bases 2 to give spiro compounds constructed between the β‐lactam and 1,3‐dioxolan‐4‐one; i.e ., the 2,3,6‐triaryl‐2‐aza‐5,7‐dioxaspiro[3.4]octane‐1,8‐diones 3 and 4 . Hydrogenation of the mixture of 3a and 4a in the presence of catalytic amount of Pd‐C produced the trans ‐2‐benzyloxy‐1,4‐diphenyl‐β‐lactam‐3‐carboxylic acid 9 .