Synthesis of containing-selenium heterocyclic new compounds

In this study, derivatives of cycloheptaselenophen-2-yl benzamide and cycloheptaselenopyrimidine having polyfunctional groups were synthesized. The synthesized compounds are thought to show biological activity.For this reason, 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-3-carbonitrile was synthesized from the reaction of malonitrile with cycloheptanone and metallic selenium by Gewald method. Treatment of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-3-carbonitrile with derivatives of benzoyl chloride generated N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-2-yl)-benzamide, N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-2-yl)-4-fluorobenzamide, N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-2-yl)-4-chlorobenzamide, N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-2-yl)-4-bromobenzamide, N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen -2-yl)-4-methoxybenzamide and N-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b] selenophen-2-yl)-4-nitrobenzamide.The reaction of synthesized 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b] selenophen-3-carbonitrile with formamide gave 6,7,8,9-tetrahydro-5H-cyclohepta[4,5]seleno[2,3-d]pyrimidin-4-amine and the reaction of synthesized 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-3-carbonitrile with formic acid gave 1,5,6,7,8,9-hexahydro-4H-cyclohepta[4,5]seleno[2,3-d]pyrimidin-4-one. 1,5,6,7,8,9-hexahydro-4H-cyclohepta[4,5]seleno[2,3-d]pyrimidin-4-one was then reacted with POCl3 to obtain 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]seleno[2,3-d]pyrimidine. Treatment of 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]seleno[2,3-d]pyrimidine with pyrrolidine generated 6,7,8,9-tetrahydro-4-(1-pyrrolidinyl)-5H-cylohepta[4,5]seleno[2,3-d]pyrimidine and treatment of 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]seleno[2,3-d]pyrimidine with morpholine generated 6,7,8,9-tetrahydro-4-(4-morpholinyl)-5H-cyclohepta[4,5]seleno[2,3-d] pirimidine. Reaction of 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]seleno[2,3-d]pyrimidine with hydrazine gave 1-hydrazino cyclohepta(b)seleno[2,3-d]pyrimidine.At the last stage of this study, 1-hydrazino cyclohepta(b)seleno[2,3-d]pyrimidine was reacted with trimethylorthoformate in order to obtain 9,10,11,12-tetrahydro-8H-cyclohepta[4,5]seleno[3,2-e]-1,2,4-triazolo[4,3-c]pyrimidine and 1-hydrazino cyclohepta(b)seleno[2,3-d]pyrimidine was reacted with NaNO2 to obtain 9,10,11,12-tetrahydro-8H-cyclohepta[4,5]seleno[3,2-e]tetrazolo[1,5-c]pyrimidine. The structures of the synthesized compounds were confirmed by spectroscopic techniques (1H-NMR, 13C-NMR, FTIR ve HR-MS) and elemental analyses.Key Words : Selenophen, Selenophenylbenzamide, Selenopyrimidine, Gewald Method