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Abstract 1,8-Naphthalenediamine reacted with dimethyl and diethyl acetylenedicarboxylates, giving rise to tetrahydronaphtho1,8-efdiazepinones (2), dihydroperimidines (3) and bis(enamino)fumarates (4). The relative yields of 3 and 4 depended on the reaction conditions, while products 2 were always very minor. Products 4, the yields of which increased considerably in the presence of a large excess of the acetylenes, underwent cyclization at 230 °C leading to quinolinoquinolinediones.
Honda et al. (Mon,) studied this question.