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Новый подход к получению 5 -трифторметилсодержащих имидазолов

Работа №106343

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химия

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Год сдачи2017
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ПРИНЯТЫЕ СОКРАЩЕНИЯ 9
ВВЕДЕНИЕ 10
1. ЛИТЕРАТУРНЫЙ ОБЗОР 11
1.1. Фторированные имидазолы и бензимидазолы 11
1.2. Синтез 2-трифторметилимидазолов, бензимидазолов и связанных с ним
аналогов 15
1.2.1. Синтез 2-перфторарилимидазолов и бензимидазолов 31
1.2.2. Синтез 2-фторимидазолов и бензимидазолов 32
1.2.3. Синтез 4- и 5-трифторметилимидазолов и аналогов 34
1.2.4. Синтез 4- и 5-фторимидазолов 55
1.2.5. Синтез 4,5,6,7-тетрафторбензимидазолов 60
1.2.6. Синтез А-фторалкилимидазолов и бензимидазолов 61
1.3. Синтез фторированных кольцом имидазолов 64
1.4. Синтез трифторметилимидазолов 69
1.5. Фторированные пурины и бензимидазолы 70
1.6. Химическая реактивность 73
1.7. Биологические свойства фторсодержащих имидазолов 73
1.8. Трифторметилимидазолы 75
1.9. Трифторметил- [ 1,2,4]триазоло [4,5-а]пиперазины 76
2. ОБСУЖДЕНИЕ РЕЗУЛЬТАТОВ 78
2.1. Синтез 1-арил-4-тозил-5-(трифторметил)-1Н-имидазолов 78
3. ЭКСПЕРИМЕНТАЛЬНАЯ ЧАСТЬ 87
3.1. Реагенты и оборудование 87
3.2. Очистка и сушка растворителей 87
3.3. Синтез исходных соединений 88
3.3.1. Типовая методика синтеза трифторацетимидоил хлоридов 89
3.4. Типовая методика синтеза бензотриазолидов 90
3.5. Типовая методика синтеза имидазолов 90
ЗАКЛЮЧЕНИЕ 94
ЛИТЕРАТУРА 95


Лидирующее место в органической химии, как в теоретическом, так и в практическом аспектах, занимают азотсодержащие гетероциклические соединения. Особенно в этом классе соединений выделяются производные биогенного гетероцикла - имидазола.
Известными примерами функциональных производных имидазола проявляющих биологическую активность являются:
• гистидин - незаменимая аминокислота;
• гистамин - медиатор серотониновых рецептор;
• лазартан - антигипертензивное средство;
• бифоназол - антимикотик;
• тризамещенный имидазол D13021 - экспериментальный противораковый препарат.
Принимая во внимание столь активный интерес к данному гетероциклу, получение новых полифункциональных производных имидазола содержащих трифторметильную группу является актуальной задачей и является целью данного исследования. 


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На основании результатов выполненного исследования можно сделать следующие выводы:
1. Впервые получены бензотриазолиды на основе трифторметилсодержащих имидоилхлоридов. Показано, что процесс алкилирования бензотриазолид иона проихсодит как по N1, так и по N2 положению с преобладанием первого.
2. Предложен простой двухкомпонентный синтез полифункциональных
1,4,5-тризамещенных имидазолов, содержащих фармокоформую трифторметильную группу, с хорошими выходами (78-92%).



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