Search academic texts

Information × Registration Number 0219U102203, 0119U102514 , R & D reports Title From the theory of azidopurine-tetrazolopurine tautomerism to its applications in medicinal and materials chemistry popup.stage_title Head Fokin Andriy A., Доктор хімічних наук Registration Date 21-12-2019 Organization National Technical University of Ukraine "Igor Sikorsky Kyiv Polytechnic Institute" popup.description2  We have demonstrated simple and efficient methods for the synthesis of 2-alkylthio-6-azidopurines and 6-alkylthio-2-azidopurines that are valuable building blocks for synthesis of target molecules required in bioorganic and medicinal chemistry. The regiochemical assignment of the obtained products was unambiguously provided by the X-ray structural analyses. For all 9-substituted azidopurine compounds, azido-tetrazolo tautomerism has been studied by experimental methods and DFT energy calculations to give a detailed insight in the structural equilibria. From the mechanistic standpoint, DFT calculations based on addition-elimination mechanism were successfully used to explain the observed the adverse reactivity trends between series of 9-substituted-2,6-dichloropurines and 9-substituted-2,6-diazidopurines. This theoretical model gave satisfactory explanations for the observed classical (C6 substitution), as well as non-classical substitution. Product Description popup.authors Gaidai Oleksandr V. Gunchenko Pavlo O. Fokin Andrii A. popup.nrat_date 2020-04-02 Close