PCl3 mediated cyclization: Synthesis, at room temperature, of N-alkenyl derivatives of 1,4-phthalazinedione

The use of a PCl3/hydrazone/dicarboxylic acid combination can be applied in an efficient one-pot procedure for the synthesis at room temperature of the title ring compounds that are also a new family of stable enamines. The phthalazinediones 7 were obtained in good yields by reaction of PCl3 with phthalic acid and hydrazones 1a,b,c containing hydrogen atoms only in one a position. Two structurally isomeric phthalazinediones (7 and 8) were obtained with hydrazones 1d,e,f,g containing hydrogen atoms in the two different a positions. When we used a methyl ketone hydrazone 1c,d,e,f,i, it was possible also to isolate the isomer containing an N-alkenyl group with two terminal hydrogen atoms. Where E,Z isomers are possible, the exclusive formation of the E isomer was always observed. As a rule, changing the order of addition of reagents gave almost identical results; however, in the case of phthalic acid, it is better to use the procedure in which PCl3 is added last to prevent the formation of the corresponding anhydride. © 1999 John Wiley & Sons, Inc.