Synthesis of Some Nitrogen Heterocycles of Medicinal Relevance
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In the first part of the project, two highly functionalized terminal alkynes, 3,3,4,4- tetraethoxybut-1-yne (TEB) and 1,1-diethoxy-but-3-yn-2-one (keto-TEB) have been used for the synthesis of 1,4-disubstituted 1,2,3-triazoles. These 1,4-disubstituted 1,2,3-triazoles have also been converted into their corresponding N-unsubstituted 1,2,3-triazoles by removing the benzyl substituent on nitrogen. Exploring the debenzylation further, a number of 1,4- and 1,5-disubstituted 1,2,3-triazoles have been synthesized and converted exclusively into the corresponding C4- monosubstituted 1,2,3-triazoles after deprotection provided the substituent on the triazole C-atom contains at least one alkoxy group. Secondly, a synthetic route for the synthesis of cis and trans 3,4-disubstituted piperidine as building blocks for the synthesis of a series of novel piperidines, has been developed. Furthermore, trans 3,4-disubstituted piperidine building block has been used for the synthesis of 1,4- and 1,5-disubstituted 1,2,3-triazoles as renin inhibitors.
Paper I: Farooq, T.; Haug, B. E.; Sydnes, L. K.; Törnroos, K. W. 1,3-Dipolar cycloadditions of benzyl azide to two highly functionalized alkynes. Monatshefte für Chemie 143(3): 505-512, March 2012. Full text not available in BORA due to publisher restrictions. The article is available at: http://dx.doi.org/10.1007/s00706-011-0691-3Paper II: Farooq, T.; Sydnes, L. K.; Törnroos, K. W.; Haug, B. E. Debenzylation of functionalized N-benzyl 4- and 5-substituted 1,2,3-triazoles. Full text not available in BORA.