Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide synPhase lanterns

Zemin Wu, Francesca Ercole, Michael FitzGerald, Senake Perera, Phil Riley, Rhonda Campbell, Yen Pham, Philip Rea, Saman Sandanayake, Marc N. Mathieu, Andrew M. Bray, Nicholas J. Ede

Research output: Contribution to journalArticleResearchpeer-review

22 Citations (Scopus)

Abstract

Solid-phase synthesis is greatly dependent on the solid support. Here, we report the use of a new hydrophilic grafted surface on SynPhase lanterns in solid-phase organic chemistry. A convenient and facile solid-phase synthesis of disubstituted 1,4-benzodiazepine-2-ones on polyamide SynPhase lanterns is described. The key step of the synthesis involved a reduction-cyclization of a nitroaryl methyl ester with a mixture of tin(II) chloride dihydrate and ammonium acetate in water and ethanol at elevated temperature to give the desired target compounds. A library of 21 disubstituted 1,4-benzodiazepine-2-ones was prepared.

Original languageEnglish
Pages (from-to)166-171
Number of pages6
JournalJournal of Combinatorial Chemistry
Volume5
Issue number2
DOIs
Publication statusPublished - 1 Mar 2003
Externally publishedYes

Cite this