RU2540080C2 - Method of selective obtaining of 1'-alkyl-1'-n-cyclohexylcarboxaamidylcyclopropa[2',3':1,9](c60-ih)[5,6]fullerenes - Google Patents

Method of selective obtaining of 1'-alkyl-1'-n-cyclohexylcarboxaamidylcyclopropa[2',3':1,9](c60-ih)[5,6]fullerenes Download PDF

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RU2540080C2
RU2540080C2 RU2013104851/04A RU2013104851A RU2540080C2 RU 2540080 C2 RU2540080 C2 RU 2540080C2 RU 2013104851/04 A RU2013104851/04 A RU 2013104851/04A RU 2013104851 A RU2013104851 A RU 2013104851A RU 2540080 C2 RU2540080 C2 RU 2540080C2
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fullerenes
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cyclohexylcarboxaamidylcyclopropa
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Усеин Меметович Джемилев
Айрат Рамилевич Туктаров
Лилия Линатовна Хузина
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Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук
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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to field of organic chemistry, namely to method of obtaining functionally substituted fullerenes, which can be applied as highly active initial substances in synthesis of medications of new generation for treatment of dangerous human diseases. method of selective obtaining of 1'-alkyl-1'-N- cyclohexylcarboxaamidylcyclopropa[2',3':1,9](C60-Ih)[5,6]fullerenes (1) is realised due to interaction of C60-fullerene with α-substituted diazoamides of formula N2C(R)C(O)NHCy (R=Me, i-Bu, -(CH2)2SMe) in o-dichlorobenzene in presence of three-component catalyst {Pd(acac)2:2PPh3:4Et3Al}, taken in molar ratio C60:diazocompound:Pd(acac)2:PPh3:Et3Al=0.01:(0.03-0.07):(0.0015-0.0025):(0.003-0.005):(0.006-0.01) Interaction is performed at temperature 80°C for 0.2-1.0 h.
EFFECT: selective obtaining of 1'-alkyl-1'-N- cyclohexylcarboxaamidylcyclopropa[2',3':1,9](C60-Ih)[5,6]fullerenes
Figure 00000009
.
1 tbl

Description

Предлагаемое изобретение относится к области органического синтеза, а именно к способу селективного получения 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллеренов общей формулы (1):The present invention relates to the field of organic synthesis, and in particular to a method for the selective production of 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] total fullerenes formulas (1):

Figure 00000001
,
Figure 00000001
,

Функционально замещенные фуллерены могут найти применение в качестве высокоактивных исходных веществ в синтезе лекарственных препаратов нового поколения для лечения опасных заболеваний человека (Л.Н.Сидоров, М.А.Юровская, А.Я.Борщевский, И.В.Трушков, И.Н.Иоффе. Фуллерены: Учебное пособие. М.: Издательство «Экзамен», 2005, 688 с.[1], Л.Б.Пиотровский, О.И.Киселев. Фуллерены в биологии, СПб.: ООО «Издательство "Росток"», 2006, 336 с. [2]).Functionally substituted fullerenes can be used as highly active starting materials in the synthesis of new generation drugs for the treatment of dangerous human diseases (L.N. Sidorov, M.A. Yurovskaya, A.Ya. Borschevsky, I.V. Trushkov, I.N. .Ioffe. Fullerenes: Textbook. M: Examination Publishing House, 2005, 688 pp. [1], LB Piotrovsky, OI Kiselev. Fullerenes in Biology, St. Petersburg: Rostock Publishing House ”, 2006, 336 p. [2]).

Известен способ (R.Gonzalez, B.W.Knight, F.Wudl. J. Org. Chem., 1994, 59, 7949 [3]) получения продукта межмолекулярной циклизации 4 в условиях реакции фуллерена C60 2 со сложными диазоамидами 3 в присутствии тетраперфторбутирата диродия [Pvh2(pfb)4] в качестве катализатора.A known method (R. Gonzalez, BWKnight, F.Wudl. J. Org. Chem., 1994, 59, 7949 [3]) to obtain the product of intermolecular cyclization 4 in the reaction of fullerene C 60 2 with complex diazoamides 3 in the presence of tetraperfluorobutyrate dirodium [ Pvh 2 (pfb) 4 ] as a catalyst.

Figure 00000002
Figure 00000002

Известный способ не позволяет получать 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллерены общей формулы (1).The known method does not allow to obtain 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] fullerenes of the general formula (1).

Известен способ (A.Skiebe, A.Hirsch. J.Chem.Soc, Chem. Commun., 1994, 335 [4]) получения смеси метано- (5) и стереоизомерных гомофуллеренов (6, 7) с общим выходом 20-30% реакцией C60-фуллерена (2) с диазоамидами в кипящем толуоле в течение 48 ч.A known method (A.Skiebe, A.Hirsch. J.Chem.Soc, Chem. Commun., 1994, 335 [4]) to obtain a mixture of methane- (5) and stereoisomeric homofullerenes (6, 7) with a total yield of 20-30 % reaction of C 60 -fullerene (2) with diazoamides in boiling toluene for 48 hours

Figure 00000003
Figure 00000003

Figure 00000004
Figure 00000004

Известный способ не позволяет селективно получать 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллерены общей формулы (1).The known method does not allow to selectively obtain 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] fullerenes of the general formula (1).

Таким образом, в литературе отсутствуют сведения по синтезу 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллеренов (1).Thus, there is no literature information on the synthesis of 1′-alkyl-1′-N-cyclohexylcarboxyamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] fullerenes (1).

Предлагается новый способ получения 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллеренов (1).A new method is proposed for the preparation of 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] fullerenes (1).

Сущность способа заключается во взаимодействии фуллерена (C60) с α-замещенными диазоамидами формулы N2C(R)C(O)NHCy (R=Me, i-Bu, -(CH2)2SMe) в о-дихлорбензоле в присутствии трехкомпонентного катализатора {Pd(acac)2:2PPh3:4Et3Al}, взятыми в мольном соотношении C60:диазосоединение:Pd(acac)2:PPh3:Et3Al=0.01:(0.03-0.07):(0.0015-0.0025):(0.003-0.005):(0.006-0.01), предпочтительно 0.01:0.05:0.002:0.004:0.008, при температуре 80°C в течение 0.2-1.0 ч.The essence of the method consists in the interaction of fullerene (C 60 ) with α-substituted diazoamides of the formula N 2 C (R) C (O) NHCy (R = Me, i-Bu, - (CH 2 ) 2SMe) in o-dichlorobenzene in the presence of ternary catalyst {Pd (acac) 2 : 2PPh 3 : 4Et 3 Al}, taken in a molar ratio of C 60 : diazo compound: Pd (acac) 2 : PPh 3 : Et 3 Al = 0.01: (0.03-0.07) :( 0.0015-0.0025 ) :( 0.003-0.005) :( 0.006-0.01), preferably 0.01: 0.05: 0.002: 0.004: 0.008, at a temperature of 80 ° C for 0.2-1.0 hours.

Получают 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9]-(C60-Ih)[5,6]фуллерены (1) с выходом 34-59%. Реакции протекают по схеме:Get 1′-alkyl-1′-N-cyclohexylcarboxaamidylcycloprop [2 ′, 3 ′: 1,9] - (C 60 -I h ) [5,6] fullerenes (1) with a yield of 34-59%. Reactions proceed as follows:

Figure 00000005
Figure 00000005

Проведение указанной реакции в присутствии палладиевого катализатора [Pd] больше 20 мол % по отношению к фуллерену C60 не приводит к существенному увеличению выхода целевого продукта (1). Применение палладиевого катализатора [Pd] в количестве меньше 20 мол % по отношению к фуллерену C60 снижает выход целевого продукта, что связано, возможно, с уменьшением реакционных центров. Реакцию следует проводить при температуре 80°C. Проведение реакции при более высокой температуре (например, 100-120°C) связано с увеличением энергозатрат, при меньшей температуре (например, 40-60°C) резко снижается скорость реакции.Carrying out this reaction in the presence of a palladium catalyst [Pd] of more than 20 mol% with respect to fullerene C 60 does not lead to a significant increase in the yield of the target product (1). The use of a palladium catalyst [Pd] in an amount of less than 20 mol% with respect to fullerene C 60 reduces the yield of the target product, which is possibly associated with a decrease in reaction centers. The reaction should be carried out at a temperature of 80 ° C. The reaction at a higher temperature (for example, 100-120 ° C) is associated with an increase in energy consumption, at a lower temperature (for example, 40-60 ° C), the reaction rate decreases sharply.

Существенные отличия предлагаемого способа:Significant differences of the proposed method:

Предлагаемый способ базируется на использовании в качестве катализатора трехкомпонентного катализатора Pd(acac)2-PPh3-Et3Al. Предлагаемый способ, в отличие от известных, позволяет селективно получать 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9]-(C60-4)[5,6]фуллерены (1), селективный синтез которых в литературе не описан.The proposed method is based on the use of a three-component catalyst Pd (acac) 2 -Ph 3 -Et 3 Al as a catalyst. The proposed method, unlike the known ones, allows one to selectively obtain 1′-alkyl-1′-N-cyclohexylcarboxaamidylcycloprop [2 ′, 3 ′: 1.9] - (C 60 -4) [5,6] fullerenes (1), selective synthesis of which is not described in the literature.

Способ поясняется примерами.The method is illustrated by examples.

К раствору 0.61 мг (0.002 ммолей) Pd(acac)2 в 0.1 мл о-ДХБ в токе сухого аргона при температуре -5°C и перемешивании добавляют 1.048 мг (0.004 ммолей) PPh3, 0.008 ммолей Et3Al и 10 мг (0.0139 ммолей) С60-фуллерена в 1 мл о-ДХБ. Реакционную массу нагревают до 80°С и по каплям добавляют 1 мг (0.01 ммолей) соответствующего диазоамида в 0.5 мл о-ДХБ. Через 0.5 ч реакционную массу охлаждают и пропускают через колонку с небольшим слоем силикагеля. Получают 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллерены (1) с выходом ~51% (по данным ВЭЖХ).To a solution of 0.61 mg (0.002 mmol) of Pd (acac) 2 in 0.1 ml of o-DCB in a stream of dry argon at a temperature of -5 ° C with stirring, 1.048 mg (0.004 mmol) of PPh 3 , 0.008 mmol of Et 3 Al and 10 mg ( 0.0139 mmol) of 60- fullerene in 1 ml of o-DCB. The reaction mass is heated to 80 ° C and 1 mg (0.01 mmol) of the corresponding diazoamide in 0.5 ml of o-DCB is added dropwise. After 0.5 h, the reaction mass is cooled and passed through a column with a small layer of silica gel. Get 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1,9] (C 60 -I h ) [5,6] fullerenes (1) with a yield of ~ 51% (according to HPLC).

Спектральные характеристики (1):Spectral characteristics (1):

Figure 00000006
Figure 00000006
Спектр ЯМР 1H (CDCl3, CS2), δ, м.д., J/Гц: 1.39 и 2.18 (м, 4Н, 2СН2), 1.52 и 1.93 (м, 4Н, 2СН2), 1.77 (м, 2Н, СН2), 2.54 (с, 3H, CH3), 4.29 (м, 1H, СН). 1 H NMR spectrum (CDCl 3 , CS 2 ), δ, ppm, J / Hz: 1.39 and 2.18 (m, 4H, 2CH 2 ), 1.52 and 1.93 (m, 4H, 2CH 2 ), 1.77 (m , 2H, CH 2 ), 2.54 (s, 3H, CH 3 ), 4.29 (m, 1H, CH). Спектр ЯМР 13C (CDCl3, CS2), δ, м.д.: 17.32, 25.46, 26.05, 33.53, 49.69, 62.00, 78.30, 138.07, 138.82, 139.33, 141.19, 141.54, 141.69, 142.04, 142.24, 142.31, 142.48, 142.83, 143.04, 143.18, 143.56, 143.71, 143.84, 143.90, 144.01, 144.13, 144.33, 144.54, 144.87, 145.23, 145.55, 146.39, 147.65, 148.32, 165.95. MALDI TOF, m/z 873.120 [M]- (C69H15NO). 13 C NMR spectrum (CDCl 3 , CS 2 ), δ, ppm: 17.32, 25.46, 26.05, 33.53, 49.69, 62.00, 78.30, 138.07, 138.82, 139.33, 141.19, 141.54, 141.69, 142.04, 142.24, 142.31 , 142.48, 142.83, 143.04, 143.18, 143.56, 143.71, 143.84, 143.90, 144.01, 144.13, 144.33, 144.54, 144.87, 145.23, 145.55, 146.39, 147.65, 148.32, 165.95. MALDI TOF, m / z 873.120 [M] - (C 69 H 15 NO).
Figure 00000007
Figure 00000007
 Спектр ЯМР 1H (CDCl3, CS2), O, м.д., J/Гц: 0.99 (д, 6Н, 2СН3, J=6.0 Hz), 1.30 (м, H, CH), 1.38 и 2.15 (м, 4Н, 2СН2), 1.51 и 1.83 (м, 4Н, 2СН2), 1.60 (м, 2Н, 1.72 (м, 2H, СН2), 4.23 (м, 1H, CH). 1 H NMR spectrum (CDCl 3 , CS 2 ), O, ppm, J / Hz: 0.99 (d, 6H, 2CH 3 , J = 6.0 Hz), 1.30 (m, H, CH), 1.38 and 2.15 (m, 4H, 2CH 2 ), 1.51 and 1.83 (m, 4H, 2CH 2 ), 1.60 (m, 2H, 1.72 (m, 2H, CH 2 ), 4.23 (m, 1H, CH). Спектр ЯМР 13C (CDCl3, CS2), δ, м.д.: 24.12, 25.30, 25.97, 26.20, 33.47, 40.34, 49.23, 63.98, 79.32, 137.95, 138.14, 138.71, 138.41, 140.51, 141.42, 141.56, 142.11, 142.19, 142.27, 142.29, 142.52, 142.90, 143.13, 143.18, 143.24, 143.51, 143.63, 143.87, 144.22, 144.78, 144.87, 145.17, 145.28, 147.32, 147.61, 148.87, 165.88. MALDI TOF, m/z 915.169 [M]- (C72H21NO). 13 C NMR spectrum (CDCl 3 , CS 2 ), δ, ppm: 24.12, 25.30, 25.97, 26.20, 33.47, 40.34, 49.23, 63.98, 79.32, 137.95, 138.14, 138.71, 138.41, 140.51, 141.42, 141.56 , 142.11, 142.19, 142.27, 142.29, 142.52, 142.90, 143.13, 143.18, 143.24, 143.51, 143.63, 143.87, 144.22, 144.78, 144.87, 145.17, 145.28, 147.32, 147.61, 148.87, 165.88. MALDI TOF, m / z 915.169 [M] - (C 72 H 21 NO).

Figure 00000008
Figure 00000008
Спектр ЯМР 1H (CDCl3, CS2), δ, м.д., J/Гц: 1.39 и 2.74 (м, 4Н, 2СН2), 1.54 и 1.88 (м, 4Н, 2СН2), 1.78 (м, 2Н, СН2), 2.14 (с, 3H, CH3), 3.12 (т, 2Н, СН2, J=7.2 Hz), 3.25 (т, 2Н, CH2, J=7.2 Hz), 4.27 (м, 1H, СН). 1 H NMR spectrum (CDCl 3 , CS 2 ), δ, ppm, J / Hz: 1.39 and 2.74 (m, 4H, 2CH 2 ), 1.54 and 1.88 (m, 4H, 2CH 2 ), 1.78 (m , 2H, CH 2 ), 2.14 (s, 3H, CH 3 ), 3.12 (t, 2H, CH 2 , J = 7.2 Hz), 3.25 (t, 2H, CH 2 , J = 7.2 Hz), 4.27 (m , 1H, CH). Спектр ЯМР 13C (CDCl3, CS2), δ, м.д.: 16.20, 25.64, 25.73, 30.17, 31.33, 33.31, 49.35, 63.82, 79.07, 137.09, 137.87, 138.10, 138.16, 139.19, 140.53, 141.44, 141.79, 142.15, 142.20, 142.26, 142.37, 142.44, 142.99, 143.16, 143.26, 143.48, 143.74, 143.90, 144.23, 144.35, 144.53, 144.80, 144.88, 145.13, 145.25, 145.39, 145.53, 14657, 147.30, 147.53, 147.85, 165.93. MALDI TOF, m/z 933.193 [M]- (C71H19NOS). 13 C NMR spectrum (CDCl 3 , CS 2 ), δ, ppm: 16.20, 25.64, 25.73, 30.17, 31.33, 33.31, 49.35, 63.82, 79.07, 137.09, 137.87, 138.10, 138.16, 139.19, 140.53, 141.44 , 141.79, 142.15, 142.20, 142.26, 142.37, 142.44, 142.99, 143.16, 143.26, 143.48, 143.74, 143.90, 144.23, 144.35, 144.53, 144.80, 144.88, 145.13, 145.25, 145.39, 145.53, 14657, 147.30, 147.53, 147.53, 147.53 , 165.93. MALDI TOF, m / z 933.193 [M] - (C 71 H 19 NOS).

Другие примеры, подтверждающие способ, приведены в табл.1Other examples confirming the method are given in table 1

Таблица 1Table 1 № п/пNo. p / p RR Мольное соотношение C60 диазосоединение: Pd(acac)2:PPh3:Et3Al, ммольThe molar ratio of C 60 diazocompound: Pd (acac) 2 : PPh 3 : Et 3 Al, mmol Время реакции, часReaction time, hour Выход целевых продуктов (1), %The yield of target products (1),%   R=MeR = Me       1one   0.01:0.05:0.002:0.004:0.0080.01: 0.05: 0.002: 0.004: 0.008 0.50.5 5151 22 0.01:0.07:0.002:0.004:0.0080.01: 0.07: 0.002: 0.004: 0.008 0.50.5 5252 33 0.01:0.03:0.002:0.004:0.0080.01: 0.03: 0.002: 0.004: 0.008 0.50.5 4444 4four 0.01:0.05:0.0025:0.005:0.010.01: 0.05: 0.0025: 0.005: 0.01 0.50.5 5959 55 0.01:0.05:0.0015:0.003:0.0060.01: 0.05: 0.0015: 0.003: 0.006 0.50.5 3434 66 0.01:0.05:0.002:0.004:0.0080.01: 0.05: 0.002: 0.004: 0.008 1.01.0 5353 77 R=/-BuR = / - Bu 0.01:0.05:0.002:0.004:0.0080.01: 0.05: 0.002: 0.004: 0.008 0.20.2 3838 99 R=-(CH2)2SMER = - (CH 2 ) 2 SME 0.01:0.05:0.002:0.004:0.0080.01: 0.05: 0.002: 0.004: 0.008 0.50.5 4747 88   0.01:0.05:0.002:0.004:0.0080.01: 0.05: 0.002: 0.004: 0.008 0.50.5 4545

Реакции проводили при температуре 80°C в o-дихлорбензоле.Reactions were carried out at a temperature of 80 ° C in o-dichlorobenzene.

Claims (1)

Способ селективного получения 1′-алкил-1′-N-циклогексилкарбоксаамидилциклопропа[2′,3′:1,9](C60-Ih)[5,6]фуллеренов (1),
Figure 00000001
,
характеризующийся тем, что C60-фуллерен взаимодействует с α-замещенными диазоамидами формулы N2C(R)C(O)NHCy (R=Me, i-Bu, -(CH2)2SMe) в o-дихлорбензоле в присутствии трехкомпонентного катализатора {Pd(acac)2:2PPh3:4Et3Al}, взятыми в мольном соотношении C60:диазосоединение:Pd(acac)2:PPh3:Et3Al=0.01:(0.03-0.07):(0.0015-0.0025):(0.003-0.005):(0.006-0.01) при температуре 80°C в течение 0.2-1.0 ч. A method for the selective preparation of 1′-alkyl-1′-N-cyclohexylcarboxamidylcycloprop [2 ′, 3 ′: 1.9] (C 60 -I h ) [5,6] fullerenes (1),
Figure 00000001
,
characterized in that the C 60 fullerene interacts with α-substituted diazoamides of the formula N 2 C (R) C (O) NHCy (R = Me, i-Bu, - (CH 2 ) 2 SMe) in o-dichlorobenzene in the presence of ternary catalyst {Pd (acac) 2 : 2PPh 3 : 4Et 3 Al}, taken in a molar ratio of C 60 : diazo compound: Pd (acac) 2 : PPh 3 : Et 3 Al = 0.01: (0.03-0.07) :( 0.0015-0.0025 ) :( 0.003-0.005) :( 0.006-0.01) at a temperature of 80 ° C for 0.2-1.0 hours.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2712046C1 (en) * 2019-08-15 2020-01-24 Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук Method for selective production of 1,2-bis-styrylfullerene

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* Cited by examiner, † Cited by third party
Title
ТУКТАРОВ А.Р. и др.: "Каталитическое циклоприсоединение диазоамидов к фуллерену С60*", Известия Академии наук. Серия химическая, 2013, N 1, с.104-106. ANDREAS SKIEBE et al.: "A facile method for the synthesis of amino acid and amido derivatives of C60", J.CHEM.SOC., CHEM.COMMUN., 1994, no.3, p.335-336 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2712046C1 (en) * 2019-08-15 2020-01-24 Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук Method for selective production of 1,2-bis-styrylfullerene

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