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Hexaazaisowurtzitane Derivatives

#4093


Development of Methods for Obtaining Hexaazaisowurtzitane Derivatives

Tech Area / Field

  • CHE-OTH/Other/Chemistry

Status
3 Approved without Funding

Registration date
13.12.2010

Leading Institute
Institute of problems of chemical-energetic technologies Siberian Branch of Russian Academy of Sciences, Russia, Altay reg., Biysk

Supporting institutes

  • Siberian Branch of RAS / Novosibirsk Institute of Organic Chemistry, Russia, Novosibirsk reg., Novosibirsk

Collaborators

  • Fraunhofer Institute Chemische Technologie, Germany, Pfinztal\nSNPE Matériaux Energétiques, France, Paris\nMACH I Inc., USA, PA, King of Prussia

Project summary

The objective of the work is to develop methods for obtaining 2,4,6,8,10,12-hexaazatetracyclo(5,5,0,03,11,05,9)dodecane derivatives, namely 2,4,6,8,10,12-hexaalkylhetaryl-, 2,4,6,8,10,12-hexaacyl derivatives and other derivatives. Such cage compounds with functional substituents in alkylhetaryl and acyl substituents should undoubtedly exhibit biological activity.

Benzyl derivatives of 2,4,6,8,10,12-hexaazatetracyclo(5,5,0,03,11,05,9)dodecane were first synthesized in 1987, by the condensation of glyoxal with the respective benzylamines. Later, it was shown that amides, alkylamines and alkylhetarylamines could react with glyoxal. However, the process of cyclization and aspects influencing upon the course of condensation of glyoxal with amines have not still studied well.

The present project suggests studying the process of condensation of glyoxal with amines, amides, hydrazine and ureas of different structure as well as to obtain compounds of hexaazaisowurtzitane structure. To identify completely the structure of obtained substances and intermediate products. To reveal aspects which affect the course of condensation reaction.

Importance and urgency of the project consists in the fact that compounds of the hexaazaisowurtzitane series, earlier used in defense industry only, will be first synthesized for the purpose of searching their biological activity.

The main results of the project will be:

  • Methods of synthesizing cage-structured polycyclic amines;
  • Development of reliable techniques of establishing structures of polycyclic derivatives and intermediate products.

The first step is to obtain primary amines and amides which may be biologically active. Preparation of these compounds in amounts ensuring further research will be carried out.

The second step is to study the process of condensation of glyoxal with selected amines, as well as to investigate chemical transformations of formed cage structures. By using advanced physicochemical methods of study, a reliable identification of intermediate and finished products of chemical interaction will be performed.

The final step is to prepare samples of hexaazaisowurtzitane structure derivatives for studying their biological activity.

The work will be fulfilled by IPCET SB RAS in collaboration with NIOCh SB RAS. The indicated institutes have stored a significant scientific and technical potential for solving a wide range of synthetic problems; they possess the necessary material and technical base. The institutes have a vast experience in conducting collaborative research.

The present work programme will allow reorienting activities of scientists, engineers and technicians working in the field of developing defense technology, upon solving problems in formulating new drugs. The collaboration with foreign partners will help integrate Russian scientists, working in the field of defense, into the world scientific community.

Foreign partners’ participation in the project is to exchange information and discuss research results. The foreign partner will have an access to all the relative detailed information in order to repeat the syntheses described.


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