Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic α-helical mimics

Laura Anderson, Mingzhou Zhou, Vasudha Sharma, Jillian M. McLaughlin, Daniel N. Santiago, Frank R. Fronczek, Wayne C. Guida, Mark L. McLaughlin

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

A facile iterative synthesis of 2,5-terpyrimidinylenes that are structurally analogous to α-helix mimics is presented. Condensation of amidines with readily prepared α,β-unsaturated α-cyanoketones gives 5-cyano-substituted pyrimidines. Iterative transformation of the 5-cyano group into an amidine allows synthesis of 2,5-terpyrimidinylenes with variable groups at the 4-, 4′-, and 4′′-positions. These compounds are designed to mimic the i, i + 4, and i + 7 sites of an α-helix.

Original languageEnglish
Pages (from-to)4288-4291
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number12
DOIs
StatePublished - Jun 18 2010

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