含窒素共役系の反応(第4報)共役1,2-Diimine類とイソシアナート類との反応

概要

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Reaction of the conjugated 1,2-diimines with isocyanates was investigated. 6,6', 7,7'-Tetramethoxy-3,3', 4,4'-tetrahydro-1,1'-biisoquinoline (I) reacted with several phenyl isocyanates (Ila-e) and benzoyl isocyanate (IIf), giving criss-cross type 1 : 2-adducts (IIIa-f). Behavior of N, N'-bis(cyclohexyl)ethylenediimine (VII) was different depending on reaction conditions. Reaction of VII with IIf at room temperature afforded 1 : 2-adduct (VIII) through 1,2-cycloaddition to C=N bond of VII, presumably due to the contribution of 1,4-dipolar structure of IIf, while in boiling xylene gave criss-cross type 1 : 2-adduct (X). On the other hand, although addition of N, N'-bis(cyclohexyl)butylene-2,3-diimine (XV) to IIf was not found to take place at room temperature, XV reacted with IIf in boiling xylene to give a criss-cross adduct (XVI) as VII.
社団法人日本薬学会の論文
1972-12-25