Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series

A range of conjugated 1,3-diynes, R¹C=CC=CR², has been prepared that incorporate the following heteroaromatic units as head groups of the substituents R¹ and/or R²: pyrimidinyl, purinyl, 2,4-diamino-1,3,5- triazinyl and acridinyl. Compounds containing the first three groups as terminal heterocyclic substituents in both R¹ and R² are bonded through methylene linkers {(CH₂)(n) n = 1, 4 or 9} to the 1,3-diyne; also reported are amphiphilic species with R² = n-C₁₀H₂₁ and a single heteroaromatic head group in chain R¹. Compounds in the acridine series are also amphiphiles and contain quaternised 1'-(9-acridinylamino)- and 1'-(6-chloro- 2-methoxyacridinylamino)- terminal substituents linked by PEG and methylene units to the diyne function. The new diynes have been synthesised by oxidative coupling of the corresponding ?-heteroaromatic functionalised 1- alkyne or by transformation of terminal groups on preformed diynes. (C) 2000 Elsevier Science Ltd.