SU445660A1 - Method for preparing 1,2-disubstituted tryptofol - Google Patents

Method for preparing 1,2-disubstituted tryptofol

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Publication number
SU445660A1
SU445660A1 SU1837904A SU1837904A SU445660A1 SU 445660 A1 SU445660 A1 SU 445660A1 SU 1837904 A SU1837904 A SU 1837904A SU 1837904 A SU1837904 A SU 1837904A SU 445660 A1 SU445660 A1 SU 445660A1
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SU
USSR - Soviet Union
Prior art keywords
disubstituted
preparing
tryptofol
aryl hydrazine
butyrolactone
Prior art date
Application number
SU1837904A
Other languages
Russian (ru)
Inventor
Игорь Иоганович Грандберг
Геннадий Петрович Токмаков
Original Assignee
Сельскохозяйственная Академия Им. К.А.Тимирязева
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Application filed by Сельскохозяйственная Академия Им. К.А.Тимирязева filed Critical Сельскохозяйственная Академия Им. К.А.Тимирязева
Priority to SU1837904A priority Critical patent/SU445660A1/en
Application granted granted Critical
Publication of SU445660A1 publication Critical patent/SU445660A1/en

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Description

Изобретение относитс  к способу получени  1,2-дизамещенных триптофолов, которые обладают биологической активностью и могут найти применение в фармацевтической практике . Известен способ получени  1,2-дизамещенных триптофолов при взаимодействии солей арилгидразина с циклическим виниловым эфиром, например дигидрофураном, при нагревании в среде апротонного растворител . Однако известный способ св зан с использованием труднодоступного сырь . С целью упрощени  процесса предлагаетс  соли арилгидразина обрабатывать а-ацил-убутиролактоном при нагревании, предпочтительно при температуре кипени  реакционной массы, в среде органического растворител , напри.мер изопропанола, в присутствии минеральной кислоты, например сол ной, с последующим выделением целевого продукта известным способом. Исходные а-ацил-у-бутилролактоны легко получают при ацилировании технического у-бутиролактона. Пример 1. 1-Бензил-2-метилтриптофол. Раствор 6,4 г (0,05 моль) а-ацетил- -бутиролактона и 11,7 г (0,05 моль) хлоргидрата а-бензилфенилгидразина в смеси 55 мл изопропанола , 30 мл воды и 5 мл концентрированной сол ной кислоты кип т т 8 час с обратным холодильником, упаривают в вакууме, добавл ют к остатку 30 мл бензола и 50 мл воды, отдел ют бензольный слой, упаривают и перегон ют остаток в вакууме. Получают 7,7 г (58%) целевого продукта, т. пл. 80-80,5°С (гексан). Найдено, %: С 81,1; Н 7,1. CisHigNO. Вычислено, %: С 81,5; Н 7,2. Примеры 2-4. Аналогично примеру 1 получают соединени , перечисленные в таблице.The invention relates to a method for producing 1,2-disubstituted tryptophols, which have biological activity and can be used in pharmaceutical practice. A known method for producing 1,2-disubstituted tryptophols by reacting aryl hydrazine salts with cyclic vinyl ether, for example dihydrofuran, when heated in an aprotic solvent medium. However, the known method involves using hard-to-reach raw materials. In order to simplify the process, it is suggested that the arylhydrazine salts be treated with a-acyl-ubutyrolactone with heating, preferably at the boiling point of the reaction mass, in an organic solvent, for example isopropanol, in the presence of a mineral acid, for example hydrochloric, and then isolating the target product in a known manner. The starting a-acyl-y-butylrolactones are easily obtained by acylation of the technical y-butyrolactone. Example 1. 1-Benzyl-2-methyltryptophol. A solution of 6.4 g (0.05 mol) of a-acetyl-β-butyrolactone and 11.7 g (0.05 mol) of a-benzylphenylhydrazine hydrochloride in a mixture of 55 ml of isopropanol, 30 ml of water and 5 ml of concentrated hydrochloric acid boil 8 hours under reflux, evaporated in vacuo, 30 ml of benzene and 50 ml of water are added to the residue, the benzene layer is separated, evaporated and the residue is distilled in vacuum. Obtain 7.7 g (58%) of the desired product, so pl. 80-80,5 ° C (hexane). Found,%: C 81.1; H 7.1. CisHigNO. Calculated,%: C 81.5; H 7.2. Examples 2-4. Analogously to Example 1, the compounds listed in the table are prepared.

Предмет изобретени Subject invention

Claims (2)

1. Способ получени  1,2-дизамещенных триптофолов на основе солей арилгидразина, отличающийс  тем, что, с целью упрощени  процесса, соль арилгидразина обрабатывают а-ацил- -бутиролактоном при нагревании в среде органического растворител , например изопропанола, в присутствии минеральной кислоты, например сол ной, с последующим выделением целевого продукта известным способом.1. A method for preparing 1,2-disubstituted aryl hydrazine salts based on aryl hydrazine salts, characterized in that, in order to simplify the process, the aryl hydrazine salt is treated with a-acyl-butyrolactone when heated in an organic solvent, such as isopropanol, in the presence of a mineral acid, for example salt, followed by separation of the target product in a known manner. 2. Способ по п. 1, отличающийс  тем, что процесс осуществл ют при температуре кипени  реакционной массы.2. A method according to claim 1, characterized in that the process is carried out at the boiling point of the reaction mass.
SU1837904A 1972-10-12 1972-10-12 Method for preparing 1,2-disubstituted tryptofol SU445660A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU1837904A SU445660A1 (en) 1972-10-12 1972-10-12 Method for preparing 1,2-disubstituted tryptofol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU1837904A SU445660A1 (en) 1972-10-12 1972-10-12 Method for preparing 1,2-disubstituted tryptofol

Publications (1)

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SU445660A1 true SU445660A1 (en) 1974-10-05

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