ONE'POT REACTION OF TRIVALENTPHOSPHORUS COMPOUNDS (Ⅰ)——A NOVEL ONE-STEP REACTION OF ADDITION,REDUCTION AND CYCLIZATION OF SUBSTITUTED β-NITROSTYRENE WITH O,O-DIALKYL PHOSPHITES
ONE'POT REACTION OF TRIVALENTPHOSPHORUS COMPOUNDS (Ⅰ)——A NOVEL ONE-STEP REACTION OF ADDITION,REDUCTION AND CYCLIZATION OF SUBSTITUTED β-NITROSTYRENE WITH O,O-DIALKYL PHOSPHITES作者机构:Institute of Elemento-Organic Chemistry Nankai University Tianjin Department of Chemistry Tianjin Normal University Academy of Military Medical Sciences Beiting
出 版 物:《Science China Chemistry》 (中国科学(化学英文版))
年 卷 期:1989年第32卷第5期
页 面:522-533页
基 金:Project supported by the National Natural Science Foundation of China. This paper was reported at CHAC Kobe Japan 1987
主 题:one-pot reaction phosphite indolephosphonate β-nitrostyrene Arbuzov rearrangement.
摘 要: In this paper the reaction of substituted β-nitrostyrene with O,O-dialkyl phosphite under cocatalysis of trimethylsilyl chloride (TMS-C1) and triethylamine (or other acidbinding agent) has been first studied and the new cyclization reaction leading to the formation of product Ⅱ, as a new class of derivatives of 1-hydroxyindoles, difficultly accessible or inaccessible with usual methods has been observed. In the related reaction it is surprising that when the Arbuzov rearrangement occurs under mild conditions, the addition, reduction and cyclization as a one-pot reaction take place simultaneously with the formation of products Ⅰ, Ⅱ, Ⅲ. By controlling the reaction conditions the products were formed almost in specificity, and thus the most interesting cyclic products Ⅱa-hcontaining phosphorus-carbon bond were obtained. Their structures were confirmed by elemental analysis, IR,1H or31p NMR and MS spectra. The crystal structure of representative compound Ⅱhwas determined by X-ray diffract