Penick Mark A, Mahindaratne Mathew P D, Gutierrez Robert D, Smith Terrill D, Tiekink Edward R T, Negrete George R
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249, USA.
J Org Chem. 2008 Aug 15;73(16):6378-81. doi: 10.1021/jo800558c. Epub 2008 Jul 16.
Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.
通过一种新的四氢萘前体的串联傅克烷基化反应，随后进行氧化芳构化，可区域选择性地得到新型二烷氧基和二羟基八氢苝。在环丁砜中，将5-烷氧基-1-四氢萘醇与对甲苯磺酸加热，以中等产率得到相应的八氢苝。在室温下，在乙腈中用路易斯酸和四氢萘-1,5-二醇进行反应，可顺利得到4,10-二羟基类似物，尽管产率有所降低。这些新系列苝类似物的例子被部分氧化为相应的连续芳香族蒽核产物，或高产率地完全芳构化为3,9-二烷氧基苝。
