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

A range of conjugated 1,3-diynes, (RC)-C-1=CC=CR2, has been prepared that i ncorporate the following heteroaromatic units as head groups of the substit uents R-1 and/or R-2 pyrimidinyl, purinyl, 2,4-diamino-1,3,5-triazinyl and acridinyl. Compounds containing the first three groups as terminal heterocy clic substituents in both R-1 and R-2 are bonded through methylene linkers {(CH2)(n), n=1, 4 or 9} to the 1,3-diyne; also reported are amphiphilic spe cies with R-2=n-C10H21 and a single heteroaromatic head group in chain R-1. Compounds in the acridine series are also amphiphiles and contain quaterni sed 1'-(9-acridinylamino)- and 1'-(6-chloro-2-methoxyacridinylamino)- termi nal substituents linked by PEG and methylene units to the diyne function. T he new diynes have been synthesised by oxidative coupling of the correspond ing omega-heteroaromatic functionalised 1-alkyne or by transformation of te rminal groups on preformed diynes. (C) 2000 Elsevier Science Ltd. All right s reserved.