REGIOCONTROLLED FORMATION OF A NOVEL DIOXADITHIAPENTACENE
REGIOCONTROLLED FORMATION OF A NOVEL DIOXADITHIAPENTACENE
复制标题
新型二氧二硫并五苯的区域控制形成
DOI：
10.1021/jo981502m
复制
发表时间：
1998
影响因子：
3.6
通讯作者：
M. Harfenist
中科院分区：
文献类型：
--
作者：
E. Boros;M. Harfenist
研究了四硫并五苯（1）的合成、晶体结构和导电性能。还描述了14，5及其6-氮杂类似物2的烷基和烷氧基取代的衍生物的合成。另一方面，相应的二恶二硫类似物实际上是未知的。C2 v对称性的子结构2是特别罕见的，并且1，3，9，11-四硝基衍生物可能是唯一已知的例子。[6]令人惊讶的是，C2 h-对称亚结构3尚未被报道。在以吩恶噻10，10-二氧化物作为潜在抗抑郁剂的药物发现努力的过程中，7，8我们观察到3的3，10-二异丙氧基衍生物的区域控制形成。本文描述了这种多环化的细节和新的环系统的X-射线晶体结构，这可能是感兴趣的研究人员在该领域的有机电荷转移络合物。3-异丙氧基吩恶噻10，10-二氧化物最近被确定为一种有效的和选择性的单胺氧化酶-A（单胺氧化酶-A）的抑制剂，这种化合物的类似物不太容易氧化代谢的兴趣。9提出了含氟衍生物的制备方法，并确定2，3-二氟-7-异丙氧基吩恶噻10，10-二氧化物为可行的目标。
The synthesis, 1, 2 crystal structure2, 3 and conductive properties2 of tetrathiapentacene (1) have been investigated. Synthesis of alkyl-and alkoxy-substituted derivatives of 14, 5 and its 6-aza analog2 have also been described. On the other hand, the corresponding dioxadithia analogues are practically unknown. Substructure 2 of C2v symmetry is particularly rare, and the 1, 3, 9, 11-tetranitro derivative may be the only known example. 6 Surprisingly, the C2h-symmetric substructure 3 has not been reported. In the course of a drug discovery effort targeting phenoxathiin 10, 10-dioxides as potential antidepressant agents, 7, 8 we observed regiocontrolled formation of the 3, 10-diisopropoxy derivative of 3. Herein are described the details of this polycyclization and the X-ray crystal structure of the new ring system, which may be of interest to researchers in the field of organic chargetransfer complexes.3-Isopropoxyphenoxathiin 10, 10-dioxide was recently identified as a potent and selective inhibitor of monoamine oxidase-A (MAO-A), and analogues of this compound less prone to oxidative metabolism were of interest. 9 The preparation of fluorinated derivatives was proposed, and 2, 3-difluoro-7-isopropoxyphenoxathiin 10, 10-dioxide was identified as a viable target.