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

W. Edward Lindsell, Christopher Murray, Peter N. Preston, T. A J Woodman

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Abstract

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.

Original languageEnglish
Pages (from-to)1233-1245
Number of pages13
JournalTetrahedron
Volume56
Issue number9
DOIs
Publication statusPublished - 25 Feb 2000

Keywords

  • 1,3,5-triazine
  • 1,3-diyne
  • Acridine
  • Purine
  • Pyrimidine

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    Edward Lindsell, W., Murray, C., Preston, P. N., & Woodman, T. A. J. (2000). Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series. Tetrahedron, 56(9), 1233-1245. https://doi.org/10.1016/S0040-4020(00)00016-8