SU833971A1 - Method of preparing 3-phenyl-2-oxo-alpha-carbolines - Google Patents

Method of preparing 3-phenyl-2-oxo-alpha-carbolines Download PDF

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Publication number
SU833971A1
SU833971A1 SU792822963A SU2822963A SU833971A1 SU 833971 A1 SU833971 A1 SU 833971A1 SU 792822963 A SU792822963 A SU 792822963A SU 2822963 A SU2822963 A SU 2822963A SU 833971 A1 SU833971 A1 SU 833971A1
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SU
USSR - Soviet Union
Prior art keywords
phenyl
carbolines
oxo
preparing
alpha
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SU792822963A
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Russian (ru)
Inventor
Натан Аронович Коган
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Ленинградский Химико-Фармацевтическийинститут
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Priority to SU792822963A priority Critical patent/SU833971A1/en
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Publication of SU833971A1 publication Critical patent/SU833971A1/en

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Description

Изобретение относитс  к новому способу получени  новых производных об-карболина, вход щих в структуру природных соединений и лекарственны веществ. Известен способ синтеза производ ных х.-карболина, основанный на реак ции взаимодействи  2-аминоиндола с. малоновым альдегидом 1 и . Недостатками метода  вл ютс  низкий выхЪд производных карболина (- 8 %) и труднодоступность малонового альдегида и 2-аминоиндола. Известен также способ получейи  9-метил-3-фенил-2-оксо-о; карболина путем взаимодействи  иодистоводород ной соли 2-аминоиндола с этиловым эфиром л-формилфенилуксусной кислоты в среде пиридина ,.3 1Недостатки способа состо т в низ ком выходе производного ot-карболина ( л/ 46 %), труднодоступности исходных реагентов, применении в качестве растворител  пиридина, сложности йыделени  полученного продукта. Цель изобретени  - разработка нового способа получени  производных 3-фенил-2-оксо-о -карболинов общей формулы jt-t V- l сл 1 i . где R - атом водорода или метоксигруппа . Указанна  цель достигаетс  нагреванием соответствукмдего азида 3-стирилиндОл-2-карбоновой кислоты до температуры разложени  азида в среде инертного органического растворител  или без него. В качестве инертного органического растворител  предпочтительно примен ют ксилол. Реакцию можно проводить также в бензоле, толуоле или других апротонных растворител х при нагревании до температуры разложени  азида 3-стирилиндол-2-карбоновой кислоты, лежащей в пределах 80-150с. Реакци  протекает по схеме Н .. СбНаThe invention relates to a new method for producing new derivatives of ob-carboline, which are included in the structure of natural compounds and drugs. A known method for the synthesis of x.-carboline derivatives based on the reaction of the interaction of 2-aminoindole with. malonic aldehyde 1 and. The disadvantages of the method are the low yield of carboline derivatives (–8%) and the inaccessibility of malonic aldehyde and 2-aminoindole. There is also known a method for preparing 9-methyl-3-phenyl-2-oxo-o; carboline by reacting the 2-aminoindole hydroiodide salt with l-formylphenylacetic acid ethyl ester in pyridine, .3 1 , the complexity of the emission of the resulting product. The purpose of the invention is to develop a new method for the preparation of 3-phenyl-2-oxo-o-carboline derivatives of the general formula jt-t V-l SL 1 i. where R is a hydrogen atom or methoxy group. This goal is achieved by heating the corresponding azide of 3-styrylindOl-2-carboxylic acid to the temperature of azide decomposition in or without an inert organic solvent. Xylene is preferably used as the inert organic solvent. The reaction can also be carried out in benzene, toluene, or other aprotic solvents by heating to the decomposition temperature of 3-styrylindole-2-carboxylic acid azide, which is in the range of 80-150 seconds. The reaction proceeds according to the scheme N.

Claims (3)

Формула изобретенияClaim 1. Способ получения З-фенил-2-οκсо-а>карболинов общей формулы СбН5 1. The method of obtaining 3-phenyl-2-οκCO-a> carbolines of the General formula SBN 5 R - атом водорода отличающи соответствующий азид 3-стирилинили метоксигрупй с я тем,R is a hydrogen atom, the corresponding corresponding azide is 3-styrylinyl or methoxy group; п. 1, о т л и ч* а ю что процесс ведут в . органического раствоп. 2, отличаючто в качестве инертгде па, что дол-2-карбоновой кислоты подвергают нагреванию до температуры разложения азида.p. 1, about l and h * a u that the process is conducted in. organic solution. 2, characterized in that it is inert that dol-2-carboxylic acid is heated to the decomposition temperature of azide. 2. Способ по щ и й с я тем, среде инертного рителя.2. A method for protecting the environment of an inert repeater. 3. Способ по щ и й с я тем, ного органического растворителя применяют ксилол.3. A method for treating an organic solvent with xylene is used.
SU792822963A 1979-07-10 1979-07-10 Method of preparing 3-phenyl-2-oxo-alpha-carbolines SU833971A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU792822963A SU833971A1 (en) 1979-07-10 1979-07-10 Method of preparing 3-phenyl-2-oxo-alpha-carbolines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU792822963A SU833971A1 (en) 1979-07-10 1979-07-10 Method of preparing 3-phenyl-2-oxo-alpha-carbolines

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SU833971A1 true SU833971A1 (en) 1981-05-30

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2823975A1 (en) * 2001-04-27 2002-10-31 Sanofi Synthelabo NEW USE OF PYRIDOINDOLONE
US7390818B2 (en) 2002-10-23 2008-06-24 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a phenyl, their preparation and their application in therapeutics
US7456193B2 (en) 2002-10-23 2008-11-25 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics
US7812165B2 (en) 2004-04-21 2010-10-12 Sanofi-Aventis 6-substituted pyridoindolone derivatives, production and therapeutic use thereof
US8063061B2 (en) 2005-10-20 2011-11-22 Sanofi-Aventis 6-heteroarylpyridoindolone derivatives, their preparation and therapeutic use thereof

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2823975A1 (en) * 2001-04-27 2002-10-31 Sanofi Synthelabo NEW USE OF PYRIDOINDOLONE
WO2002087574A3 (en) * 2001-04-27 2003-02-13 Sanofi Synthelabo Use of pyridoindolone derivatives for preparing anticancer medicines
US7524857B2 (en) 2001-04-27 2009-04-28 Sanofi-Aventis Pharmaceutical combinations based on pyridoindolone derivatives and anticancer agents
US7390818B2 (en) 2002-10-23 2008-06-24 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a phenyl, their preparation and their application in therapeutics
US7456193B2 (en) 2002-10-23 2008-11-25 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics
US7816368B2 (en) 2002-10-23 2010-10-19 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics
US8012991B2 (en) 2002-10-23 2011-09-06 Sanofi-Aventis Pyridoindolone derivatives substituted in the 3-position by a phenyl, their preparation and their application in therapeutics
US7812165B2 (en) 2004-04-21 2010-10-12 Sanofi-Aventis 6-substituted pyridoindolone derivatives, production and therapeutic use thereof
US8063061B2 (en) 2005-10-20 2011-11-22 Sanofi-Aventis 6-heteroarylpyridoindolone derivatives, their preparation and therapeutic use thereof

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