Convenient Synthesis of 2-Amino-1,8-naphthyridines, Building Blocks for Host-Guest and Self-Assembling Systems

Edward E. Fenlon, Thomas J. Murray, Monica H. Baloga, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26% yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4%) of 2,6-diaminopyridine-3,5-dicarboxaldehyde. Alternatively, conversion of 2,6-diaminopyridine to 2,6-bis(pivaloylamino)pyridine (6), directed lithiation with n-butyllithium, treatment with N-formylmorpholine, and hydrolysis produced 4 in 67% overall yield. The Friedländer condensation of 4 with a variety of activated and unactivated ketones afforded 2-amino-1,8-naphthyridines and bis(2-amino-1,8-naphthyridines) in moderate to good yields, providing a convenient synthesis of useful building blocks for new host-guest and self-assembling systems.

Original languageEnglish
Pages (from-to)6625-6628
Number of pages4
JournalJournal of Organic Chemistry
Volume58
Issue number24
DOIs
StatePublished - 1 Jan 1993
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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