Production of 3-benzoyl-2,1 -benzisoxazoles, 2-phenyl-4H-3,1 -benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate

Benjamin Staskun*, Theodorus Van Es

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3.1 -benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2- phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.

Original languageEnglish
Pages (from-to)511-516
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
DOIs
Publication statusPublished - 1993

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