НОВЫЕ ДОСТИЖЕНИЯ В СИНТЕЗЕ ЦИКЛОАЛКА[b]ИНДОЛОВ
Аннотация
В обзоре обобщены данные о синтезе соединений, остовом которых служит гетероцикл циклоалка[b]индольного строения. Рассмотрены подходы к синтезу гомологичных структур, начиная от аннелированного карбоциклического фрагмента с тремя атомами углерода до восьмичленных аналогов. Представлены примеры циклизаций, в том числе с наведением хиральных центров с использованием соответствующих каталитических систем, с различной энантио- и диастереоселективностью. Уделено внимание реакциям карбоциклизации, протекающим в присутствии комплексов металлов, алкилатов лития, меж- или внутримолекулярного циклоприсоединения алленов, активированных алкенов с 1,3-диполярофилами или диеноподобными системами. При получении циклопропа[b]индолов наиболее часто используются реакции [2+1]-циклоприсоединения индолов с различными карбенами, в подходах к синтезу индолов, аннелированных с циклобутаном применение находят реакции [2+2]-циклоприсоединения. Для получения индолов, к которым 2,3-аннелированы карбоциклы средних размеров, эффективно используются синтетические приемы, включающие применение в качестве исходных веществ производных индола, 3-нитроиндола, внутри- и межмолекулярные реакции 3-этинил-, 3-алленил-, 3-алкенил- или функционализированных 2-алкизамещенных индолов в присутствии комплексов палладия, золота, родия, меди, серебра, индия, фосфорорганических кислот и их амидов, трифторэтанола, гексафторизопропанола, органических сульфо- или трифторуксусной кислот. Известны методы фотохимического воздействия, приводящие к циклопента[b]индолам. При получении этих гетероциклов успешно используются реакции циклоприсоединения 1,3-диполей, генерируемых из (2-индолил)диарилметанолов, к диполярофилам. Не менее эффективны реакции циклоприсоединения производных 2-винилиндола к активированным алкенам или карбонильным соединениям в присутствии различных катализаторов, приводящие к ди- или тетрагидрокарбазолам или их семичленным гомологам. Одним из часто используемых подходов для получения циклоалка[b]индолов являются реакции, основанные на катализируемых превращениях индолзамещенных циклопропанов или межмолекулярном взаимодействии циклопропанов с индолами в различных условиях.
Для цитирования:
Гатауллин Р.Р. Новые достижения в синтезе циклоалка[b]индолов. Изв. вузов. Химия и хим. технология. 2023. Т. 66. Вып. 2. С. 6-22. DOI: 10.6060/ivkkt.20236602.6720.
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