Reactivity of n-aryl-α, α-dichlorinated arylketimines

Structure and reactivity in highly halogenated ketazines

“…By contrast, in the fully halogenated azines 9,12, and 13 separation of the o peaks from the others was very much less (the phenyl peakof 12 was a singlet); their Ph nmr absorptions are also given in Table 1. A similar collapse of the ring aryl protons to a singlet has been observed in the spectrum of a,a-dichloroalkylarylketimines (9).…”

“…There was no clear evidence of the presence of the expected azine of phenylmethylglyoxal, 28. Related chemistry describing the reactions of a,a-dichloroalkylarylketimines with NaOMeMeOH was similarly complex, mixtures of unsaturated halogenated and methoxylated ketones being produced (9). In light of the well-established synthesis of ketones by reaction of Grignard reagents with simple ortho esters (RC(OEt)3 + RIMgX+ RC(R1)(OEt)z+ RCOR') an alternative route to 28 from the trimethoxy compound 16 seemed feasible.…”

A facile one-pot synthesis of tetrahydropyrimidines part 3 Synthesis of [alkanediylbis(3-alkyl/aralkyl/aryl-3,6-dihydropyrimidine-1,5(2H)-diyl)bis(arylmethanones) and [1,4-phenylenebis(3-phenyl-3,6-dihydropyrimidine-1,5(2H)-diyl)]bis(phenylmethanone)

“…for C 39 H 40 N 4 O 2 (596.76): C,78.49;H,6.76;N,9.39. Found: C,78.30;H,6.64;N,5 7.19-7.29 (m, 6H), 7.31-7.45 (m, 10H), 7.48-7.51 (m, 6H); ms: m/z 611 (MH + ).…”

“…[1,5 3, 66.2, 110.6, 118.6, 119.3, 121.5, 124.5, 125.7, 128.2, 128.4, 129.8, 130.3, 142.9, 146.0, 193 ,6.57;N,9.61. Found: C,78.61;H,6.66;N,5 8,47.7,50.8,58.1,65.7,107.1,127.5,128.6,128.9,129.2,129.7,130.5,135.7,140.2,150.3,192.6. Anal.…”

“…The starting materials 1a [5], 1b [6], 1c [7] and 1e-f [8] were prepared by reported procedures. The unknown starting material 1d was prepared by reported procedure [8] and its analytical and spectral data are given below.…”