Synthesis of 1,3-Diynes in the Purine, Pyrimidine, 1,3,5-Triazine and Acridine Series

✍ Scribed by W. Edward Lindsell; Christopher Murray; Peter N. Preston; Thomas A.J. Woodman

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 261 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00016-8

✦ Synopsis

A range of conjugated 1,3-diynes, R 1 CxCCxCR 2 , has been prepared that incorporate the following heteroaromatic units as head groups of the substituents 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 heterocyclic substituents in both R 1 and R 2 are bonded through methylene linkers {(CH 2 ) n , n1, 4 or 9} to the 1,3-diyne; also reported are amphiphilic species with R 2 n-C 10 H 21 and a single heteroaromatic head group in chain R 1 . Compounds in the acridine series are also amphiphiles and contain quaternised 1 H -(9-acridinylamino)-and 1 H -(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 v-heteroaromatic functionalised 1-alkyne or by transformation of terminal groups on preformed diynes.