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Safar Poghosyan

Speaker for catalysis 2017 - Safar Poghosyan

Title: Regioselective synthesis of spiroheterooxoindolines

Safar Poghosyan

National Academy of Sciences of the Republic of Armenia, Armenia

Biography

S.A. Poghosyan was born on 1.09.1946 in the Republic of Armenia. After finishing the local secondary school in 1963, he entered the chemical deparment of Yerevan State University. In 1968 he graduated from the University with the gualification “Organic Chemistry’’. In 1969 he joined the post graduate studies at the Instute of Fine Organic Chemistry of the National Academy of Sciences, RA. In1975 he defended his thesis. From 1972 to 1978 he worked in the same Institute as a junior researcher, since 1978 as a senior researcher.   
The fields of his researcher are synthesis of pentacyclic benz(g)indoloindolizines,
ß-carbolines  spirocondensed with indoline. Since 1988 he has been working in the Llaboratory of Synthesis of Spiroheterocyclic Compounds. He has about 100 publications (10 authoric works). Repeatedly spoke at confererences. He has been carrying out the investigations in the field of synthesis of heterospirocyclic compounds, containing nitrogen, oxygen.
 

Abstract

One of the most urgent tasks of modern organic chemistry is the creation and study of new domino processes that make it possible to obtain almost inaccessible hetero-organic compounds with a minimal number of stages and with maximum economic efficiency. Domino-reaction [1] is a process, involving two or more reactions with the formation of a bond, proceeding under identical conditions, each subsequent transformation being carried out according to the functional groups that have arisen as a result of the preceding reaction. Domino-reactions make it possible to obtain new heterocycles without using multistage and hard-to-implement methods of synthesis and provide the maximum economic effect.  
Oxoindoline derivatives have a wide spectrum of pharmacological activity, and are also important intermediates in the synthesis of many indole and other compounds [2-13]. To a large extent, this is due to the diverse biological activity of many natural compounds that play an important role in maintaining the vital activity of animals and plant organisms. 
The known methods do not allow to synthesize the above spiroheterocycles because of difficult-to-implement methods, so the development of new synthesis routes for these compounds is relevant in modern organic chemistry.
We have developed a new improved domino-reaction for the synthesis of the above spiro compounds by boiling a mixture of isatins with C-H acids in the presence of catalytic amounts of bases. To explore the limits of the new preparative method application, as starting components were used, on the one hand, various isatins, on the other - containing methylene groups cyanoacetic ester,  dimedone or 3,3-dimethyl-5-(phenylimino) cyclohexanone. It should be noted that the three-component condensation of isatins with two components having an active methylene group, proceeds according to the principle of cascade cyclization and is a regioselective method for the synthesis of the above-mentioned spiro-condensed oxoindolines.