Braunstein Pierre, Siri Olivier, Taquet Jean-Philippe, Yang Qing-Zheng
Laboratoire de Chimie de Coordination, UMR 7513 CNRS Université Louis Pasteur, 4, rue Blaise Pascal, 67070 Strasbourg Cédex, France.
Chemistry. 2004 Aug 6;10(15):3817-21. doi: 10.1002/chem.200400244.
Their pH-controlled reactivity places the N,N'-dialkyl-2-amino-5-lithium alcoholate-1,4-benzoquinonemonoimines [C(6)H(2)(NHCH(2)R') (=NCH(2)R')(=O)(OLi)] 7 (R'=tBu) and 8 (R'=p-C(6)H(4)-tBu) at the crossroads of a new versatile strategy for the preparation of two very different classes of substituted quinones. We describe new 2-(N-alkyl)amino-5-hydroxy-1,4-benzoquinones, which are parent molecules to biologically active substituted aminobenzoquinones, for which changes of the N-substituent will become readily possible. The results of the first X-ray structural determination of such compounds ([C(6)H(2)(NHCH(2)tBu)(OH)(=O)(2)] 13) are also reported and we compare the influence of the number of N-substituents of the C(6) ring on the supramolecular networks resulting from self-assembling of 13, zwitterionic N,N'-dineopentyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium [C(6)H(2)(=NHCH(2)tBu)(2)(=O)(2)] 9 and N,N',N",N"'-tetraneopentyl-2,5-diamino-1,4-benzoquinone diimine [C(6)H(2)(NHCH(2)tBu)(2)(=NCH(2)tBu)(2)] 15.
它们的pH控制反应性使N，N'-二烷基-2-氨基-5-锂醇盐-1，4-苯醌单亚胺[C(6)H(2)(NHCH(2)R')(=NCH(2)R')(=O)(OLi)] 7（R'=叔丁基）和8（R'=对-C(6)H(4)-叔丁基）处于制备两类截然不同的取代醌的新通用策略的交叉点。我们描述了新的2-(N-烷基)氨基-5-羟基-1，4-苯醌，它们是生物活性取代氨基苯醌的母体分子，对于这些分子，N-取代基的变化将变得容易实现。还报道了此类化合物（[C(6)H(2)(NHCH(2)叔丁基)(OH)(=O)(2)] 13）的首次X射线结构测定结果，并且我们比较了C(6)环上N-取代基数对由13、两性离子N，N'-二新戊基-2-氨基-5-醇盐-1，4-苯醌单亚胺鎓[C(6)H(2)(=NHCH(2)叔丁基)(2)(=O)(2)] 9和N，N'，N"，N"'-四新戊基-2，5-二氨基-1，4-苯醌二亚胺[C(6)H(2)(NHCH(2)叔丁基)(2)(=NCH(2)叔丁基)(2)] 15自组装形成的超分子网络的影响。
