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

Research output: Contribution to journalArticle

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

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Diynes
Acridines
Triazines
Amphiphiles
Alkynes
Polyethylene glycols
pyrimidine
purine

Keywords

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

Cite this

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
Edward Lindsell, W. ; Murray, Christopher ; Preston, Peter N. ; Woodman, T. A J. / Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series. In: Tetrahedron. 2000 ; Vol. 56, No. 9. pp. 1233-1245.
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Edward Lindsell, W, Murray, C, Preston, PN & Woodman, TAJ 2000, 'Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series', Tetrahedron, vol. 56, no. 9, pp. 1233-1245. https://doi.org/10.1016/S0040-4020(00)00016-8

Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series. / Edward Lindsell, W.; Murray, Christopher; Preston, Peter N.; Woodman, T. A J.

In: Tetrahedron, Vol. 56, No. 9, 25.02.2000, p. 1233-1245.

Research output: Contribution to journalArticle

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AU - Murray, Christopher

AU - Preston, Peter N.

AU - Woodman, T. A J

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