Синтез дигидротиадиазолов и дигидротиадиазинов,конденсированных с азолами тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Гапоненко, Наталья Игорьевна

• Гапоненко, Наталья Игорьевна
• кандидат химических наук
• 2012

Оглавление диссертации кандидат химических наук Гапоненко, Наталья Игорьевна

Введение.

Глава 1. Методы синтеза конденированных 1,3,4-тиадиазинов и 1,3,4тиадиазолов (литературный обзор).

1.1. Синтез конденсированных 1,3,4-тиадиазинов.

1.1.1. Взаимодействие с а-галогенкарбонильными соединениями.

1.1.2. Взаимодействие с галогеннитрилами.

1.1.3. Взаимодействие с карбонильными соединениями.

1.1.4. Взаимодействие с дигалогенидами.

1.1.5 Другие методы синтеза.

1.2 Синтез конденсированных 1,3,4-тиадиазолов.

1.2.1 Синтез исходя из Ы-амино-а-меркаптогетероциклов.

1.2.1.1 Взаимодействие с карбонильными и карбоксильными соединениями.

1.2.1.2 Взаимодействие с галогенкарбонильными соединениями.

1.2.1.3 Взаимодействие с ароматическими и активированными нитрилами, цианобромидом.

1.2.1.4 Внутримолекулярная циклизация тиоэфиров 4-амино-1,2,4-триазолов.

1.2.1.5 Взаимодействие с изоцианатами, изотиоцианатами и тиоцианатами.

1.2.1.6 Взаимодействие с реагентом Вильсмайера.

1.2.1.7 Взаимодействие с сероуглеродом.

1.2.1.8 Взаимодействие с дигалогенидами.

1.2.1.9 Транслокационая перегруппировка.

1.2.1.10 Взаимодействие с орто-эфирами.

1.2.1.11 Реакции с производными этилена и ацетилена.

1.2.2 Синтез исходя из 1,3,4-тиадиазолов.

1.2.3 Другие методы синтеза.

Глава 2. Синтез дигидротиадиазолов и дигидротиадиазинов, конденсированных с азолами (обсуждение результатов).

2.1. Синтез 2,3-дигидроимидазо[2,1-6][1,3,4]тиадиазолов и 2,3-дигидро [1,3,4]тиадиазоло [3,2-а] бензимидазолов.

2.2. Синтез 3,4-дигидро-2Я-[1,3,4]тиадиазино[3,2-а]бензимида-золов.

2.3. Синтез спирановых 3,4-дигидро-2#-[1,3,4]тиадиазино[3,2-я] бензимидазолов.

2.4. Синтез гидроксииндено[1,3,4]тиадиазинов и [1,4]тиазинов.

2.5 Биологическая активность синтезированных производных

Глава 3. Экспериментальная часть.

Выводы.

Заключение диссертации по теме «Органическая химия», Гапоненко, Наталья Игорьевна

выводы.

1. Разработан общий метод аннелирования тиадиазольного кольца к азотистым гетероциклам, заключающийся в реакции внутримолекулярной циклизации бензилтио- и фенацилтиопроизводных бензимидазолилиминов и имидазолилиминов.

2. Доказано, что формирование пятичленного цикла при алкилировании фенацилгалогенидами о-индотиофенола, о-индоанилина, имидазолил- и бензимидазолилиминов не зависит от природы конденсированной системы.

3. Установлено, что определяющим фактором формирования тиадиазольного цикла является ароматизация циклогексадиенонового фрагмента Э-метиленпроизводных имидазолил- и бензимидазолилиминов.

4. Найден общий метод синтеза широкого спектра неизвестных ранее производных 3,4-дигидро-2Я-[1,3,4]тиадиазино[3,2-а]бензимидазолов, основанный на образовании тиадиазинового цикла за счет формирования связи углерод - углерод на завершающей стадии циклизации. Обнаружено, что протекание циклизации в большей степени зависит от подвижности протонов б'-метиленовой группы, чем от природы заместителей иминного фрагмента.

5. Показано, что реакция аннелирования тетрагидротиадиазинового цикла является удобным подходом к получению спирановых бензимидазолотиадиазинов. Выявлена высокая диастереоселективность процесса внутримолекулярной циклизации.

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