SU255277A1 - METHOD FOR PRODUCING DERIVATIVES OF BENZOKARBAZOLA The invention relates to the field of obtaining new compounds that can be used in the synthesis of biologically active substances. The proposed method of obtaining benzocarbazole derivatives of the formula R - P, Alk, Ar, R - Alk consists in the fact that 2-benzyl-5- methoxyindolyl-3-carboxylic acid or its ester of the formula R'OX ^^ ^ COOR "\ A ^ J-CH2-C6H5, where R is H, Alk, Ar; R" —H, Alk; R '—Alk; subjected to intramolecular cyclization in the presence of cyclizing agents, such as polyphosphoric acid, followed by isolation of the obtained product in a known manner. Example 1. 1,4-Dihydro-4-keto-6-methoxy - Google Patents
METHOD FOR PRODUCING DERIVATIVES OF BENZOKARBAZOLA The invention relates to the field of obtaining new compounds that can be used in the synthesis of biologically active substances. The proposed method of obtaining benzocarbazole derivatives of the formula R - P, Alk, Ar, R - Alk consists in the fact that 2-benzyl-5- methoxyindolyl-3-carboxylic acid or its ester of the formula R'OX ^^ ^ COOR "\ A ^ J-CH2-C6H5, where R is H, Alk, Ar; R" —H, Alk; R '—Alk; subjected to intramolecular cyclization in the presence of cyclizing agents, such as polyphosphoric acid, followed by isolation of the obtained product in a known manner. Example 1. 1,4-Dihydro-4-keto-6-methoxyInfo
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- SU255277A1 SU255277A1 SU1232048A SU1232048A SU255277A1 SU 255277 A1 SU255277 A1 SU 255277A1 SU 1232048 A SU1232048 A SU 1232048A SU 1232048 A SU1232048 A SU 1232048A SU 255277 A1 SU255277 A1 SU 255277A1
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- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11H-benzo[a]carbazole Chemical class C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 title description 9
- 229920000137 polyphosphoric acid Polymers 0.000 title description 5
- 239000000126 substance Substances 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 title description 2
- 150000002148 esters Chemical class 0.000 title description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 title description 2
- 238000002955 isolation Methods 0.000 title description 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 230000002194 synthesizing Effects 0.000 title 1
- 229960000583 Acetic Acid Drugs 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000994 depressed Effects 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Пример 2. 1,4-Дигидро-4-кето-6-метокси9-метил (2,3)бензокарбазол (циклизацией 1метил-2-бецзил-5-метоксциндолил-3 - карбоновой кислоты).Example 2. 1,4-Dihydro-4-keto-6-methoxy9-methyl (2,3) benzocarbazole (by cyclization of 1-methyl-2-benzyl-5-methoxycindol-3 - carboxylic acid).
Дл оиыта берут 5 г (0,017 моль) 1-метил2-бензил-5-метоксииндолил-3-карбоновой кислоты и 250 г полифосфорной кислоты. Реакцию и выделеиие вещества провод т в услови х примера 1. Выход 1,4-дигидро-4-кето-6метокси-9-метил (2,3)бензокарбазола 4,3 г (93,5%); т. пл. 153-154°С (из лед ной уксусной кислоты).5 g (0.017 mol) of 1-methyl 2-benzyl-5-methoxyindolyl-3-carboxylic acid and 250 g of polyphosphoric acid are taken for analysis. The reaction and release of the substance is carried out under the conditions of Example 1. The yield of 1,4-dihydro-4-keto-6methoxy-9-methyl (2,3) benzocarbazole is 4.3 g (93.5%); m.p. 153-154 ° С (from glacial acetic acid).
Найдено, %: ,С 78,02; 77,68; Н 5,50; 5,50; N 5,02; 5,04.Found,%: C 78.02; 77.68; H 5.50; 5.50; N 5.02; 5.04.
CisHisNOa.CisHisNOa.
Вычислено, %; С 77,95; Н 5,45; N 5,05.Calculated,%; C 77.95; H 5.45; N 5.05.
Пример 3. 1,4-Дигидро-4-кето-6-метокси9-метил (2,3)бензокарбазол (циклизацией метилового эфира 1-метил-2-бензил-5-метоксииндолил-3-карбоновой кислоты).Example 3. 1,4-Dihydro-4-keto-6-methoxy9-methyl (2,3) benzocarbazole (cyclization of 1-methyl-2-benzyl-5-methoxyindolyl-3-carboxylic acid methyl ester).
В трехгорлую колбу, снабженную механической мешалкой, хлоркальциевой трубкой, помещают 50 г полифосфорной кислоты и 1 г (0,003 моль) метилового эфира 1-метил-2-бензил-5-метоксииндолил-З-карбоновой кислоты. Реакционную смесь энергично перемешивают при комнатной температуре 6 час и оставл ют на ночь. Затем раствор медленно выливают при перемешивании и охлаждении льдом в 4-5-кратный объем воды. Выделившийс осадок отфильтровывают, промывают насыщенным раствором бикарбоната натри , затем водой до нейтральной реакции и суша г. Выход 1,4-дигидро-4-кето-6-метокси-9-метил (2,3)бензокарбазола после перекристаллизации из лед ной уксусной кислоты 0,65 г (73%); т. пл. 152-153°С; соединение не дает депрессии с 1,4-дигидро-4-кето-6-.метокси-8метил (2,3)бензокарбазолом из примера 2.In a three-necked flask equipped with a mechanical stirrer, a calcium chloride tube, 50 g of polyphosphoric acid and 1 g (0.003 mol) of 1-methyl-2-benzyl-5-methoxyindolyl-3-carboxylic acid methyl ester are placed. The reaction mixture is stirred vigorously at room temperature for 6 hours and left overnight. Then the solution is slowly poured with stirring and cooling with ice in 4-5-fold volume of water. The precipitate was filtered off, washed with saturated sodium bicarbonate solution, then with water until neutral and dried. The yield of 1,4-dihydro-4-keto-6-methoxy-9-methyl (2,3) benzocarbazole after recrystallization from glacial acetic acid 0.65 g (73%); m.p. 152-153 ° C; the compound is not depressed with 1,4-dihydro-4-keto-6-.methoxy-8methyl (2,3) benzocarbazole from example 2.
Пример 4. 1,4-Дигидро-4-кето-6-метокси9-фенил (2,3) бензокарбазол.Example 4. 1,4-Dihydro-4-keto-6-methoxy9-phenyl (2,3) benzocarbazole.
Дл опыта берут 2 г (0,0054 моль метилового эфира 1-фенил-2-бензил-5-метоксииндолил-3-карбоновой кислоты и 100 г полифосфорной кислоты. Реакционную смесь энергично перемешивают при комнатной температуре 7 час. Выделение вещества провод т в услови х примера 3. Выход 1,4-дигидро-4-кето-бметокси-9-фенил (2,3) бензокарбазола после перекристаллизации из смеси метанол-этилацетат (3:1) 0,7 г (39%); т. пл. 140,5- 141,5°С.For the experiment, 2 g (0.0054 mol of 1-phenyl-2-benzyl-5-methoxyindolyl-3-carboxylic acid methyl ester and 100 g of polyphosphoric acid) are taken. The reaction mixture is vigorously stirred at room temperature for 7 hours. The substance is isolated under conditions of x of example 3. The yield of 1,4-dihydro-4-keto-bmetoxy-9-phenyl (2,3) benzocarbazole after recrystallization from methanol-ethyl acetate (3: 1) 0.7 g (39%); mp. 140.5-141.5 ° C.
Пайдено, %: С 81,19; 81,24; Н 5,10; 4,98; N 4,04; 3,99.Paydeno,%: C 81.19; 81.24; H 5.10; 4.98; N 4.04; 3.99.
СазНпМОг.SazNPMOG.
Вычислено, %: С 81,36; Н 5,05; N 4,12.Calculated,%: C 81.36; H 5.05; N 4.12.
Предмет изобретени Subject invention
Способ получени производных бензокарбазола формулыThe method of obtaining benzocarbazole derivatives of the formula
R ОR o
где R -Н, Alk, Аг; R-Alk, отличающийс тем, что 2-бензил-5-метоксииндолил-3-карбо30 новую кислоту или ее эфир формулыwhere R is H, Alk, Ar; R-Alk, characterized in that 2-benzyl-5-methoxyindolyl-3-carboxy30 new acid or its ester of the formula
R ОR o
,COOR, COOR
СНг-СбНзSNG-SbNz
I RI r
где R -Н, Alk, Аг; R -Alk; R -Н, Alk; подвергают внутримолекул рной циклизации в присутствии циклизующих агентов, например полифосфорной кислоты, с последующим выделением полученного продукта известным способом.where R is H, Alk, Ar; R-Alk; R-H, Alk; subjected to intramolecular cyclization in the presence of cyclizing agents, for example polyphosphoric acid, followed by isolation of the obtained product in a known manner.
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| SU255277A1 true SU255277A1 (en) |
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