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An improved protocol for the preparation of 5,11-dialkyl-6,12-di(hetero)aryl-5,11-dihydroindolo[3,2-b]carbazoles and synthesis of their new 2,8-dicyano- / 2,8-bis(benzo[d]thiazol-2-yl)-substituted derivatives
ARKIVOC Pub Date : 2018-06-17 , DOI: 10.24820/ark.5550190.p010.557 Roman A. Irgashev , Nikita A. Kazin , Gennady L. Rusinov , Valery N. Charushin
ARKIVOC Pub Date : 2018-06-17 , DOI: 10.24820/ark.5550190.p010.557 Roman A. Irgashev , Nikita A. Kazin , Gennady L. Rusinov , Valery N. Charushin
A number of 5,11-dialkyl-6,12-di(hetero)aryl-5,11-dyhydroindolo[3,2-b]carbazoles has been synthesized by modified method based on HBr catalyzed condensation of (hetero)aromatic aldehydes with indole in MeCN solution affording 5,6,11,12-tetrahydroindolo[3,2-b]carbazoles, that have been aromatized with I2 in DMF solution for 1 h at reflux, followed by alkylation of 5,11-dihydro compounds. New 2,8-dicyano(10 examples) as well as 2,8-bis(benzo[d]thiazol-2-yl)-substituted (5 examples) derivatives of these 5,11-dyhydroindolo[3,2b]carbazoles have been obtained through their initial C2,8-formylation, followed by treatment of dialdehydes with excess of hydroxylamine and dehydration of the formed aldoximes with acetic anhydride or by interaction with excess of 2-aminothiophenol in DMSO solution, respectively.
中文翻译:
5,11-二烷基-6,12-二(杂)芳基-5,11-二氢吲哚并[3,2-b]咔唑的制备及其新2,8-二氰基-/2的合成的改进方案, 8-双(苯并[d]噻唑-2-基)-取代的衍生物
通过基于 HBr 催化(杂)芳香醛与吲哚在 MeCN 溶液中得到 5,6,11,12-四氢吲哚并[3,2-b]咔唑,其在 DMF 溶液中与 I2 在回流下芳构化 1 小时,然后将 5,11-二氢化合物烷基化。这些 5,11-二氢吲哚并[3,2b]咔唑的新 2,8-二氰基(10 个实例)以及 2,8-双(苯并[d]噻唑-2-基)-取代(5 个实例)衍生物具有分别通过它们最初的 C2,8-甲酰化,然后用过量的羟胺处理二醛和用乙酸酐脱水或通过与过量的 2-氨基苯硫酚在 DMSO 溶液中的相互作用而获得。
更新日期:2018-06-17
中文翻译:
5,11-二烷基-6,12-二(杂)芳基-5,11-二氢吲哚并[3,2-b]咔唑的制备及其新2,8-二氰基-/2的合成的改进方案, 8-双(苯并[d]噻唑-2-基)-取代的衍生物
通过基于 HBr 催化(杂)芳香醛与吲哚在 MeCN 溶液中得到 5,6,11,12-四氢吲哚并[3,2-b]咔唑,其在 DMF 溶液中与 I2 在回流下芳构化 1 小时,然后将 5,11-二氢化合物烷基化。这些 5,11-二氢吲哚并[3,2b]咔唑的新 2,8-二氰基(10 个实例)以及 2,8-双(苯并[d]噻唑-2-基)-取代(5 个实例)衍生物具有分别通过它们最初的 C2,8-甲酰化,然后用过量的羟胺处理二醛和用乙酸酐脱水或通过与过量的 2-氨基苯硫酚在 DMSO 溶液中的相互作用而获得。