SU859368A1 - Method of preparing1,2,3,4,5,6,7,12,12b-octahydro-2,4-dioxoindolo/2,3-a/quinolysin (its versions) - Google Patents

Method of preparing1,2,3,4,5,6,7,12,12b-octahydro-2,4-dioxoindolo/2,3-a/quinolysin (its versions) Download PDF

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SU859368A1
SU859368A1 SU792859061A SU2859061A SU859368A1 SU 859368 A1 SU859368 A1 SU 859368A1 SU 792859061 A SU792859061 A SU 792859061A SU 2859061 A SU2859061 A SU 2859061A SU 859368 A1 SU859368 A1 SU 859368A1
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USSR - Soviet Union
Prior art keywords
octahydro
dioxoindolo
tetrahydro
quinolysin
carbolinyl
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SU792859061A
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Russian (ru)
Inventor
Афанасий Андреевич Ахрем
Юрий Германович Чернов
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Институт Биоорганической Химии Ан Белорусской Сср
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Priority to SU792859061A priority Critical patent/SU859368A1/en
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Publication of SU859368A1 publication Critical patent/SU859368A1/en

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Description

(54) СПОСОБ ПОЛУЧЕНИЯ ,3,4/6,7,12,(54) METHOD OF OBTAINING, 3.4 / 6,7,12,

12В-ОКТАГИДРО-Э, 4-ДИОКСОИНДОЛО 2,3-al ХИНОЛИЗИНА (ЕГО ВАРИАНТЫ) Изобретение относитс  к способу получени  1,2,-3,,7,12,12в-октагидро-2 ,4-диоксоиндоло 2,3-а хин зина формулы который  вл етс  промежуточным продуктом в синтезе аналогов Н-С COOCjHs выход продукта 35%. Исходное соединение III получаетс  в результате сложного шестистадийного синтеза из диэтилацетондикарбоксилата с общим .выходом 33% 1. 0 1 in иохимбина и реалкалоидов р да зеопина. Известен способ получени  1,2,3, 4,6,7f12,12в-oктaгидpo-2,4-диoкcoиндoлo 2 , 3-а хинолизина взаимодействием триптамина II с 4-корбозтокси-3-этилендиоксимасл ным альдегидом III при кип чении в лед ной уксусной кислоте. Вьщеленное промежуточное основание Шиффа IV затем циклизуют обработкой этанольным раствором хлорис;гого водорода. COOCiHs Недостатками указанного способа  вл ютс , таким образом, невысокий выход целевого продукта и примейелке в синтезе труднодоступного исходного соединени .12B-OCTAGIDRO-E, 4-DIOXOINDOLO 2,3-al CHINOLYSINA (ITS OPTIONS) The invention relates to a method for producing 1,2, -3, 7,12,12-octahydro-2, 4-dioxoindo 2,3-a A quinzine of the formula which is an intermediate product in the synthesis of H-C COOCjHs analogs yields a 35% yield. The starting compound III is obtained as a result of a complex six-step synthesis from diethylacetone dicarboxylate with a total yield of 33% 1. 0 1 in yohimbine and realkaloids p and zeopin. A method of obtaining 1,2,3, 4,6,7f12,12 in-octahydro-2,4-dioxoindo-2, 3-a quinolysin by reacting tryptamine II with 4-corbozotoxy-3-ethylenedioxy-aldehyde III at boiling in ice acetic acid. The precipitated Schiff IV intermediate base is then cyclized by treatment with an ethanolic solution of chloris; gogo hydrogen. COOCiHs The disadvantages of this method are, therefore, the low yield of the target product and the primer in the synthesis of a difficult-to-access starting compound.

Цель изобретени  - повышение выхода и упрощение процесса.The purpose of the invention is to increase the yield and simplify the process.

Поставленна  цель достигаетс  тем, что 3,4-дигидро-ГЬ-карболин подвергсиот взаимодействию с диметилацетондикарбоксилатом в органическом растворителе и обрабатывают выделен - ный промежуточный диметил-et- 1,2,3,4тетрагидро-fi- карболинил- (1) J -ацетондикарбоксилат последовательно водными растворами щелочи и кислоты.The goal is achieved by the fact that 3,4-dihydro-Gb-carboline is subjected to interaction with dimethylacetone dicarboxylate in an organic solvent and the isolated intermediate dimethyl-et-1,2,3,4 tetrahydro-fi-carboline-1 (1) J-acetone dicarboxylate is treated consistently with aqueous solutions of alkali and acid.

В качестве органического растворител  используют бензол.Benzene is used as an organic solvent.

Процесс протекает по следующей схеме;The process proceeds as follows;

Claims (3)

Формула изобретенияClaim 1. Способ получения 1,2,3,4,6,7,1. The method of obtaining 1,2,3,4,6,7, 15 12,12в-октагидро-2,4-диоксоиндоло[2,15 12,12b-octahydro-2,4-dioxoindolo [2, 3—а]хинолизина, отличающийс я тем, что, ,с целью повышения выхода и упрощения процесса, 3,4-дигидро- β- карболин подвергают взаимо20 действию с метиловым эфиром ацетондикарбоновой кислоты в органическом растворителе и выделенный промежуточный диметил -cL· -[1,2,3,4-тетрагидро-р-карболинил-(1)1-ацетондикарбоксилат обрабатывают последовательно водными растворами щелочи и кис(лоты.3-a] quinolysin, characterized in that, in order to increase the yield and simplify the process, 3,4-dihydro-β-carboline is reacted with methyl acetone dicarboxylic acid in an organic solvent and the isolated intermediate dimethyl-cl · - [ 1,2,3,4-tetrahydro-p-carbolinyl- (1) 1-acetone dicarboxylate is treated sequentially with aqueous solutions of alkali and acid (lots. 2. Способ поп. 1, отличают и й с я тем, что в качестве ор- jq ганического растворителя используют бензол.2. The method of pop. 1, they are distinguished by the fact that benzene is used as the organic solvent. 3. Способ получения 1,2,3,4,6,7, 12,12в-октагидро-2,4-диоксоиндоло[2,3а]хинолизина, о тличающийс я тем, что, с целью повышения выхода и упрощения процесса, 3,4-дигидро-(ь- карболин подвергают взаимодействию с ацетондикарбоновой кислотой в водном метаноле, выделенную промежуточную γ-[1,2,3,4-тетрагидро-й-карболинил-(1)1 ацетоуксусную кислоту обрабатывают метанольным раствором хлористого водорода, полученный метиловый эфир гидрохлорида [1,2,3,4-тетрагидро-Й-карболинил(1)]ацетоуксусной кислоты обрабатывают водным аммиаком.3. The method of obtaining 1,2,3,4,6,7, 12,12-octahydro-2,4-dioxoindolo [2,3a] quinolizine, characterized in that, in order to increase the yield and simplify the process, 3 , 4-dihydro- (b-carboline) is reacted with acetone dicarboxylic acid in aqueous methanol, the isolated intermediate γ- [1,2,3,4-tetrahydro-th-carbolinyl- (1) 1 acetoacetic acid is treated with a methanol solution of hydrogen chloride, obtained [1,2,3,4-tetrahydro-Y-carbolinyl (1)] acetoacetic acid hydrochloride methyl ester is treated with aqueous ammonia.
SU792859061A 1979-12-26 1979-12-26 Method of preparing1,2,3,4,5,6,7,12,12b-octahydro-2,4-dioxoindolo/2,3-a/quinolysin (its versions) SU859368A1 (en)

Priority Applications (1)

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SU792859061A SU859368A1 (en) 1979-12-26 1979-12-26 Method of preparing1,2,3,4,5,6,7,12,12b-octahydro-2,4-dioxoindolo/2,3-a/quinolysin (its versions)

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Application Number Priority Date Filing Date Title
SU792859061A SU859368A1 (en) 1979-12-26 1979-12-26 Method of preparing1,2,3,4,5,6,7,12,12b-octahydro-2,4-dioxoindolo/2,3-a/quinolysin (its versions)

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