Метил-2-(4-ацетил-5-метилиден-2-фенил-2,5-дигидрооксазол-2-ил)-2-бромацетат (24d)

Соединение (RS, RS)-24d (80 мг, 57%) и соединение (RS, SR)-24d (40 мг, 28%) были получены по общей методике из азадиена 4s (141 мг, 0.4 ммоль).

Соединение (RS, RS)-24d. Бесцветное маслообразное вещеcтвo. Спектр ЯМР 1Н (400 МГц, CDCl3), δ, м. д.: 2.65 c (3Н, СН3), 3.59 с (3Н, СH3), 4.95 с (1Н, СН), 5.07 д (1Н, СН, J 2.3 Гц), 5.25 д (1Н, СН, J 2.3 Гц), 7.36–7.44 м (3Н, Hаром), 7.61–7.64 м (2Н, Hаром). Спектр ЯМР 13С (100 МГц, CDCl3), δ, м. д.: 27.6, 51.0, 53.0, 90.6, 107.8, 126.4, 128.5, 129.4, 136.2, 155.9, 159.8, 166.2, 194.5. HRMS (ESI-TOF) вычислено для С15Н14BrNO4Na+ [M+Na]+: 373.9998; найдено: 374.0007.

Соединение (RS, SR)-24d. Бесцветное маслообразное вещеcтвo. Спектр ЯМР 1Н (400 МГц, CDCl3), δ, м. д.: 2.68 c (3Н, СН3), 3.64 с (3Н, СH3), 4.88 с (1Н, СН), 4.99 д (1Н, СН, J 2.4 Гц), 5.24 д (1Н, СН, J 2.4 Гц), 7.40–7.45 м (3Н, Hаром), 7.60–7.63 м (2Н, Hаром). Спектр ЯМР 13С (100 МГц, CDCl3), δ, м. д.: 27.6, 51.8, 53.0, 90.4, 108.3, 126.5, 128.5, 129.5, 136.9, 155.0, 160.5, 166.1, 194.6. HRMS (ESI-TOF) вычислено для С15Н14BrNO4Na+ [M+Na]+: 373.9998; найдено: 374.0007.

Этил-2-(2-оксоэтил-2-этокси)-2-метил-5-метилиден-2,5-дигидрооксазол-4-карбоксилат 24е

Соединение 24е (80 мг, 78%) было получено по общей методике из азадиена Z-4zj (102 мг, 0.4 ммоль).

Соединение 24е. Бесцветное маслообразное вещеcтвo. Спектр ЯМР 1Н (400 МГц, CDCl3), δ, м. д.: 1.24 т (3Н, СН3, J 7.2 Гц), 1.42 т (3Н, СН3, J 7.2 Гц), 1.66 с (3Н, СH3), 2.88 и 2.92 (2Н, АВ-к, J 15.3 Гц), 4.13 к (2Н, СН2, J 7.2 Гц), 4.43 к (2Н, СН2, J 7.2 Гц), 4.78 д (1Н, СН, J 2.3 Гц), 5.09 д (1Н, СН, J 2.3 Гц). Спектр ЯМР 13С (100 МГц, CDCl3), δ, м. д.: 14.0 (2C), 25.5, 43.3, 60.7, 62.5, 88.1, 108.0, 155.7, 156.0, 160.1, 168.1. HRMS (ESI-TOF) вычислено для С12Н17NO5Na+ [M+Na]+: 278.0999; найдено: 278.0994.

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Метил-2-бром-2-[5-метил-5-(пиперидин-1-ил)-2,4-дифенил-2,5-дигидрооксазол-2-ил]ацетат (25)

К раствору азадиена 4zа (154 мг, 0.4 ммоль) в безводном CH2Cl2 (3 мл) добавили при перемешивании пиперидин (68 мг, 0.8 ммоль). После 30 мин растворитель испарили в вакууме, а остаток очищали колоночной хроматографией на силикагеле с использованием элюента смеси Et2O-гексан (от 1:30 до 1:10) в качестве. В результате получили (RS, RS)-25а (46 мг, 30%), (RS, SR)-25а (15 мг, 10%) и соединение 25 в виде смеси диастереомеров (dr = 1.5:1).

Соединение 25. Бесцветное кристаллическое вещество, т. пл. 118–130; 146–153 °С (Et2O-гексан). Спектр ЯМР 1Н (300 МГц, CDCl3), δ, м. д.: 1.25 с (3Н, СН3), 1.49–1.69 м (6Н, 3СН2), 2.55–2.70 м (2Н, СН2), 2.95–3.17 м (2Н, СН2),3.68 с (3Н, СH3), 4.66 с и 4.76 с (1Н, 2СН), 7.30–7.37 м (3Н, Hаром), 7.40–7.56 м (3Н, Hаром), 7.65–7.77 м (2Н, Hаром). Спектр ЯМР 13С (75 МГц, CDCl3), δ, м. д.: 23.9, 24.0, 24.6, 24.7, 26.4, 47.7, 47.8, 52.3, 52.5, 52.6, 53.4, 103.0, 103.4 107.0, 127.1, 127.3, 127.5, 128.0, 128.2, 128.3, 128.8, 128.9, 130.3, 130.4, 131.5, 139.5, 167.36, 167.4, 169.6, 170.0 (6 сигналов 13С перекрывается). HRMS (ESI-TOF) вычислено для С24Н27BrN2O3Na+ [M+Na]+: 493.1097; найдено: 493.1097.

5. ВЫВОДЫ

Rh(II)-Катализируемые реакции б-диазокарбонильных соединений с алкил-2-бром/2-хлор-2Н-азирин-2-карбоксилатами или с 4-бром-/4-хлор-/4-иод-5-алкоксиизоксазолами является удобным методом синтеза электронодефицитных 4-бром-/4-хлор-/4-иод-2-азабута-1,3-диенов. Электронодефицитные 4-галоген-2-азабута-1,3-диены способны претерпевать термическую обратимую 1,4-электроциклизацию в 3-галоген-2,3-дигидроазеты, которая может служить методом синтеза функционально замещенных 3-галоген-2,3-дигидроазетов. Для ее реализации необходимо наличие двух сильных электроноакцепторных заместителя при атоме С1 и ароматического или гетероароматического заместителя при атоме С1. Доля дигидроазетовой формы растет в ряду I > Br > Cl, а также с увеличением электронодонорной способности заместителя при атоме C1. Енолизуемые 1-ацил-2-азабута-1,3-диены в условиях нуклеофильного/основного катализа при комнатной температуре или в нейтральной среде при повышенных температурах претерпевают 1,5-экзо-триг-циклизацию в 5-алкилиден-2,5-дигидрооксазолы, которые могут быть получены с высокими входами.

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