SU833971A1 - Method of preparing 3-phenyl-2-oxo-alpha-carbolines - Google Patents
Method of preparing 3-phenyl-2-oxo-alpha-carbolines Download PDFInfo
- 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
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- carbolines
- oxo
- preparing
- alpha
- Prior art date
Links
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
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)
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 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU833971A1 true SU833971A1 (en) | 1981-05-30 |
Family
ID=20852031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU792822963A SU833971A1 (en) | 1979-07-10 | 1979-07-10 | Method of preparing 3-phenyl-2-oxo-alpha-carbolines |
Country Status (1)
Country | Link |
---|---|
SU (1) | SU833971A1 (en) |
Cited By (5)
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 |
-
1979
- 1979-07-10 SU SU792822963A patent/SU833971A1/en active
Cited By (9)
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SU833971A1 (en) | Method of preparing 3-phenyl-2-oxo-alpha-carbolines | |
SU837321A3 (en) | Method of preparing prostaglandine derivatives | |
KR20010022595A (en) | Process for preparing l-ascorbic acid | |
CN114835652B (en) | Method for synthesizing iminobenzotriazole compound under photocatalysis condition | |
US5777136A (en) | Process for the glycosidation of colchicine derivatives and the products obtained thereby | |
SU564813A3 (en) | Method for obtaining derivatives of indoloquinolysine or their salts | |
Satoh et al. | Photochemical Synthesis of 6-Aryluridines1 | |
FI73680B (en) | PROCEDURE FOR THERAPEUTIC VERIFICATION OF 5,11-DIHYDRO-11 - / (4-METHYL-1-PIPERAZINYL) -ACETYL / -6H-PYRIDO / 2,3-B // 1,4 / BENZODIAZEPIN-6-ON. | |
JPS5699450A (en) | Preparation of n-acyl-n-substituted formamide derivative | |
Schwarz et al. | NMR spectroscopic investigation of p-substituted 2, 4, 4, 6-tetraphenyl-1, 4-dihydropyridines and their oxa and thia analogues | |
SU745898A1 (en) | Method of preparing di-n-hydroxysuccinimide ester of succinic acid | |
SU628819A3 (en) | Method of producing derivatives of tetrahydrothienopyridine | |
Kiely et al. | Six-Membered Nitrogen Heterocycles from Xylaramide and Ribaramide | |
Hay et al. | A regio-and stereocontrolled method for preparing 3, 3-diarylacrylamides | |
SU819103A1 (en) | Method of preparing 5-aminobenzofurazan | |
SU1015823A3 (en) | Process for preparing tautomers of dl-5-amino-4,5,6,7-tetrahydro-1h-indazole and dl-s-amino-4,5,6,7 tetrahydro-2h-idazole | |
SU578007A3 (en) | Method of preparing proscillaridine derivatives | |
Di Gregorio et al. | Mono-and polyanhydride formation by reaction of 2, 2, 4, 4, 6, 6-hexachlorotriazatriphosphorine with carboxylic acid salts under mild conditions | |
SU743992A1 (en) | Method of preparing 4,4'-azobis-(1-bromo-4-cyanopentane) | |
SU1456428A1 (en) | Method of producing 4-dicyanomethylene-2-methyl-6-dimethylaminostyryl-4-(n)-pyrane | |
RU2238272C1 (en) | Method for preparing 1-alkyl-6,6-dimethyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1h-indole-3-spiro-2-( 1-aryl-3-aroyl-4-hydroxy-5-oxo-2,5-dihydropyrrols) | |
JPH075554B2 (en) | Process for producing 5-bromopyridone-3-carboxamide compound | |
SU548611A1 (en) | Method for preparing 3-chloro-3,4-dihydro-1,2,3-diazaphosphol | |
SU1634669A1 (en) | Process for preparing 4-amino-5-tosyl-imidazo (1,2:1,6) pyrido (2,3) pyrazine | |
JPS5813590B2 (en) | anthraquinone |