STUDIES ON PHOSPHONIUM YLIDES-XXII. THE BEHAVIOR OF 3,4-DIPHENYL-5-CYANOPYRIDAZINE-6-THIONE TOWARD PHOSPHORUS YLIDES. NEW SYNTHESIS OF FUROPYRIDAZINE DERIVATIVES
作者:Leila S. Boulos、Hoda A. Abdel-Malek
DOI:10.1080/10426500490257087
日期:2004.1
4-Diphenyl-5-cyanopyridazine-6-thione (1) reacts with carbethoxy-methylene and carbmethoxymethylene-triphenylphosphoranes (2a,b) to give both the olefinic compounds (3a,b) and 3,4-diphenyl-6-alkoxyfuro-[3,2-c]-pyridazines (4a,b) respectively. Treatment of 1 with phosphorus ylide (2c) afforded only the new furopyridazine (4c). On the other hand, when (1) reacts with diphenylmethylenetriphenylphosphorane (2d), adduct
3,4-二苯基-5-氰基哒嗪-6-硫酮 (1) 与 carbethoxy-methylene 和 carboxymethylene-triphenylphosphoranes (2a,b) 反应生成烯烃化合物 (3a,b) 和 3,4-diphenyl-6-分别为烷氧基呋喃-[3,2-c]-哒嗪 (4a,b)。用磷叶立德 (2c) 处理 1 只得到新的呋喃哒嗪 (4c)。另一方面,当(1)与二苯基亚甲基三苯基膦(2d)反应时,加合物(5)与三苯基膦一起得到。此外,将试剂 (2e) 应用于 (1) 得到新产品 3,4-二苯基-6-(苯基亚氨基)-5-氰基哒嗪 (6)。讨论了新产品形成的机制,并根据分析和光谱数据介绍了产品的可能结构。