СИНТЕЗ N-ГИДРОКСИИНДОЛОВ
Аннотация
В данном обзоре рассмотрены основные синтетические подходы для получения N-гидроксииндолов. Первый подход заключается во внутримолекулярной восстановительной циклизации орто-замещенных нитроароматических соединений различными химическими восстановителями. В качестве субстратов для синтеза N-гидроксииндолов используются 2-нитрофенилацетальдегиды (синтез по Ачесону), N,N-дизамещенные амино-2-нитростиролы (синтез по Сомею), орто-нитрокетоэфиры различного строения или 1-(o-нитроарил)-1-цианоалкены, орто-нитрокетоны, орто-нитрофенилацетонитрилы. В качестве восстановителей применяются треххлористый титан, цинк либо в присутствии хлористого аммония, либо в уксусной кислоте, двухлористое олово, а также водород с использованием катализаторов на основе благородных металлов (платина, палладий). Вторым подходом является [3+2]-циклоприсоединение нитрозоароматических соединений к алкинам или дезоксигенирование орто-замещенных нитроароматических соединений с последующей внутримолекулярной циклизацией. Третий подход представляет собой каталитическое окисление 2,3-дигидроиндолов или индолов различного строения концентрированной перекисью водорода в присутствии каталитических количеств вольфрамата натрия. Особое внимание уделено синтезу функциональных производных N-гидроксииндол-5,6-дикарбоновых кислот. Это обусловлено тем, что данные соединения, как правило, синтезируют из коммерчески доступного сырья без использования дорогостоящих катализаторов, применяя хорошо известные и отработанные методы синтеза. При этом удалось получать индолы различного дизайна, которые, например, могут являться основными билдинг-блоками для синтеза БАВ, фталоцианинов различного строения, обладающих жидкокристаллическими и каталитическими свойствами. Представители этого класса гетероциклов встречаются среди многочисленных природных соединений, могут быть использованы в качестве терапевтических агентов, например, как ингибиторы человеческой лактатдегидрогеназы изоформы 5, селективные ингибиторы моноаминооксидазы А и Б, а N-метоксииндолы могут применяться для лечения рака молочной железы.
Для цитирования:
Чиркова Ж.В. Синтез N-гидроксииндолов. Изв. вузов. Химия и хим. технология. 2017. Т. 60. Вып. 4. С. 4-20.
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