1,2,4-TRIAZINES IN ORGANIC SYNTHESIS. 8. INTRAMOLECULAR DIELS–ALDER REACTION OF 5-ACYL-1,2,4-TRIAZINEOXIME ETHERS. NEW ROUTE OF SYNTHESIS OF ALKYLHETARYLKETONES

Abstract

Intramolecular diene cycloaddition of 5-acyl-1,2,4-triazineoxime ethers involving a dienophile substituent in the 3-position of the triazine ring is studied. New alkylhetarylketones are synthesized by hydrolysis of the condensed N- and O-containing heterocyclic products. The starting materials are prepared by oxidation of 5-acetyl- and 5-butyryl-3-methylthio-1,2,4-triazineoxime ethers with KMnO4 to the sulfonyl derviatives with subsequent replacement of the CH3SO2 group by sodium 3-butyn-1-oxide, 4-pentyn-1-oxide and o-cyanophenoxide.

Authors: T. Lipińska, D. Branowska, and A. Rykowski.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (3), pp 334-342

http://link.springer.com/article/10.1007/BF02259365