The reaction between 4‐dimethylaminopyridine (DMAP) and 2‐bromoacetophenone(s) readily gives 1‐ [2‐(4‐substitutedphenyl)‐2‐oxoethyl]‐4‐(dimethylamino)pyridinium bromide (1–14). Action of aqueous NaOH on 1–8 generates the corresponding pyridinium ylide (15–22), which is isolated as a colored stable crystalline solid. Addition of 15–22 to dimethylacetylene dicarboxylate (DMAD) gives dimethyl 3‐(substitutedbenzoyl)‐7‐(dimethylamino)indolizine‐1,2‐dicarboxylate (23–30) in 46–62% yield.
In both of the title compounds, C(23)H(19)ClN(2)O, (I), and C(23)H(18)Cl(2)N(2)O, (II), the molecular packing is influenced by weak intermolecular C-H.O and C-H.pi interactions, but despite the chemical similarity of the compounds, the packing in (II) is entirely different from that observed in (I).
In the title compound, C15H15Cl2N2O+·Br−, the angle between the least‐squares planes of the dichlorophenyl moiety and the pyridine ring is 20.23 (9)°. The molecular packing is mainly influenced by intermolecular C—H⋯Br hydrogen‐bond interactions. The molecules form an extended chain along the b axis, through C—H⋯Br hydrogen bonds.
Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.002 A Ê R factor = 0.045 wR factor = 0.134 Data-to-parameter ratio = 16.6For details of how these key indicators were automatically derived from the article, see
Key indicatorsSingle-crystal X-ray study T = 160 K Mean '(C±C) = 0.003 A Ê R factor = 0.038 wR factor = 0.101 Data-to-parameter ratio = 21.4For details of how these key indicators were automatically derived from the article, see
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